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Tianjin Kind Pharma Co., Ltd.

Factory direct sales, accept customization. Lifitegrast is API for the treatment of signs and symptoms of dry eye, a syndrome called keratoconjunctivitis sicca. Kind Pharma has its own laboratory, we can do analytical testing for API (Active Pharma

Lifitegrast 99%

Cas:1025967-78-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Saiwante (shanghai) New Material Technology Co., Ltd.

Boiling Point:811.9±65.0 °C(Predicted) PKA:3.14±0.10(Predicted) PSA:142.37000 Density:1.479±0.06 g/cm3(Predicted) LogP:6.17690 Storage Temp.:Hygroscopic, -20°C Freezer, Under inert atmosphere Solubility.:DMS

Hot selling Lifitegrast(SAR 1118) 1025967-78-5

Cas:1025967-78-5

Min.Order:1 Gram

FOB Price: $2.0 / 5.0

Type:Trading Company

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Jinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pu

1025967-78-5

Cas:1025967-78-5

Min.Order:1 Gram

FOB Price: $1.0

Type:Manufacturers

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Koning Pharmchem Co., Ltd.

KONING PHARMCHEM CO., LTD. has committed itself to a strategy of providing a unique service for companies involved in the manufacture of pharmaceuticals, healthcare products, food, cosmetics and other fine chemicals. Our products including but not li

Lifitegrast

Cas:1025967-78-5

Min.Order:0

Negotiable

Type:Trading Company

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Wuhan Fortuna Chemical Co.,Ltd

Unique advantages of Lifitegrast Cas 1025967-78-5 Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White powder Storage:cool dry place Package:1kg/foil bag;25kg/drum Application:med

Manufacturer high quality Lifitegrast Cas 1025967-78-5 with good price

Cas:1025967-78-5

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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Hangzhou Think Chemical Co. Ltd

Lifitegrast CAS No.:1025967-78-5 Name: Lifitegrast Synonyms: N-[[2-(6-Benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-L-phenylalanine; SAR 1118

High purity Lifitegrast CAS No.:1025967-78-5

Cas:1025967-78-5

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Lifitegrast

Cas:1025967-78-5

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Manufacturer supply CAS 1025967-78-5 with competitive price

Cas:1025967-78-5

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Product Name Lifitegrast Alias ifitegrast;CS-2633;Lifitegrast(API);SAR-1118;SAR1118;Lifitegrast-d4;Lifitegrast Impurity;lifitegrast;Lifitegrast, SAR 1118 CAS No. 1025967-78-5 Molecular Formula C29H2

Lifitegrast CAS:1025967-78-5

Cas:1025967-78-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufactu

Lifitegrast CAS 1025967-78-5

Cas:1025967-78-5

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

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HANWAYS CHEMPHARM CO.,LIMITED

Wuhan hanweishi Pharmchem Co., Ltd(Hanways chempharm) is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The leading products range are APIs, Hormones, Peptides

Lifitegrast CAS 1025967-78-5

Cas:1025967-78-5

Min.Order:100 Kilogram

FOB Price: $1.0 / 5.0

Type:Trading Company

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Shanghai Minstar Chemical Co., Ltd

lifitegrast Chemical Properties Boiling point 811.9±65.0 °C(Predicted) density 1.479±0.06 g/cm3(Predicted) pka 3.14±0.10(Predicted) lifitegrast Chemical Properties Boiling point 811.9±65.0 °C(Predi

lifitegrast.

Cas:1025967-78-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Qingdao Beluga Import and Export Co., LTD

lifitegrast CAS: 1025967-78-5 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermedia

lifitegrast CAS: 1025967-78-5

Cas:1025967-78-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

lifitegrast

Cas:1025967-78-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

lifitegrast

Cas:1025967-78-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

99.78% Pharmaceutical Raw Materials Lifitegrast CAS NO.1025967-78-5

Cas:1025967-78-5

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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Hubei Yuanmeng Biological Technology Co., Ltd.

Hubei Yuanmeng Biological Technology Co., Ltd., which is located in Wuhan, China. We are specializing in the exportation of APIs, and plant extracts ect. Our products has been exported to America, Australia, Brazil, the Europe, Middle East and other

High Purity lifitegrast CAS 1025967-78-5 with Fast Shipment

Cas:1025967-78-5

Min.Order:1 Kilogram

FOB Price: $3.0 / 5.0

Type:Trading Company

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Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

SAR-1118 Lifitegrast 1025967-78-5

Cas:1025967-78-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

LIFITEGRAST

Cas:1025967-78-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

lifitegrast

Cas:1025967-78-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Hefei Zhaobo Technology Co., Ltd.

Our Advantages Production: Advanced chemical equipment with years of experience.Staffs for producing various extract products. Quality Control:A complete set of Testing Professional and Analysis Equipment ensures the Quality Requirements and Speci

Lifitegrast CAS 1025967-78-5

Cas:1025967-78-5

Min.Order:1 Kilogram

FOB Price: $150.0 / 180.0

Type:Trading Company

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Lifitegrast

Cas:1025967-78-5

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov

99.78% Pharmaceutical Raw Materials Lifitegrast CAS NO.1025967-78-5

Cas:1025967-78-5

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

Chemvon Biotechnology Co. Ltd.

Chemvon Biotechnology Co. Ltd., established in the end of 2004, is a high-technology pharmaceutical and fine chemical company in R&D, manufacturing and sales of Lifitegrast . With the experience and specialization in technology of asymmetric sy

Lifitegrast

Cas:1025967-78-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Sinoway Industrial Co., Ltd.

Why is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c

99% up GMP DMF lifitegrast powder 1025967-78-5

Cas:1025967-78-5

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 6 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

1025967-78-5 lifitegrast

Cas:1025967-78-5

Min.Order:1 Kilogram

FOB Price: $1000.0

Type:Lab/Research institutions

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Siwei Development Group Ltd.

Product name: Lifitegrast CAS No.:1025967-78-5 Molecule Formula:C29H24Cl2N2O7S Molecule Weight:615.48 Purity: 99.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTING ITEMS

Best Quality Lifitegrast with good supplier

Cas:1025967-78-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

Lifitegrast (This product is only available in Japan.)

Cas:1025967-78-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

lifitegrast

Cas:1025967-78-5

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

99.78% Pharmaceutical Raw Materials Lifitegrast CAS NO.1025967-78-5

Cas:1025967-78-5

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Synthetic route

lifitegrast dicyclohexylamine salt

lifitegrast dicyclohexylamine salt

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
With phosphoric acid In dichloromethane; water at 50℃; for 0.5h;96%
((S)-benzyl 2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-methylsulfonyl)phenyl)propanoate
1194550-67-8

((S)-benzyl 2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-methylsulfonyl)phenyl)propanoate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
With formic acid; palladium 10% on activated carbon; triethylamine In tetrahydrofuran; methanol at 20℃; for 4h;95%
With formic acid; palladium 10% on activated carbon; triethylamine In tetrahydrofuran; methanol Reagent/catalyst; Solvent;n/a
With lithium hydroxide monohydrate In water; acetone at -5 - 0℃; for 1h; Reagent/catalyst; Solvent; Temperature;
With hydrogenchloride In water; acetonitrile at 3 - 25℃; for 19.5h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;3.8 g
2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid

2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid

(S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid

(S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Stage #1: 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid With [2-(1H-indol-3-yl)-ethyl]-methylamine; N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 40℃; for 2h; Inert atmosphere;
Stage #2: (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid In tetrahydrofuran at 20 - 30℃;
92%
Stage #1: 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid With triethylamine In N,N-dimethyl-formamide at 28℃; for 0.166667h;
Stage #2: With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 5 - 8℃; for 2h;
Stage #3: (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid In N,N-dimethyl-formamide at 8℃; for 1h;
(S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid

(S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid

3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Stage #1: (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid; 3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylate With N-ethyl-N,N-diisopropylamine In acetonitrile at 40 - 45℃;
Stage #2: With hydrogenchloride In water at 0 - 5℃; for 1h; pH=5;
87%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20 - 45℃; for 4h;
benzofuran-6-carboxylic acid
77095-51-3

benzofuran-6-carboxylic acid

(S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
851785-70-1

(S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -10 - 20℃; Reagent/catalyst; Solvent; Temperature;83.8%
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 10 - 20℃; for 1.5h;
C30H26Cl2N2O7S

C30H26Cl2N2O7S

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 25 - 30℃; for 3h; Reagent/catalyst; Solvent;80%
C19H12Cl3NO3

C19H12Cl3NO3

(S)-2-amino-3-(3-(methylsulphonyl)phenyl)propanoic acid hydrochloride

(S)-2-amino-3-(3-(methylsulphonyl)phenyl)propanoic acid hydrochloride

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Stage #1: (S)-2-amino-3-(3-(methylsulphonyl)phenyl)propanoic acid hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;
Stage #2: C19H12Cl3NO3 In dichloromethane at 0 - 5℃; Temperature; Inert atmosphere;
77%
(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid
82278-73-7

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: copper(l) iodide; caesium carbonate; L-proline / dimethyl sulfoxide / 9 h / 100 °C
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C
3: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 0 °C
4: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
5: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
7: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: copper(l) iodide; caesium carbonate; L-proline; sodium methansulfinate / dimethyl sulfoxide / 9 h / 95 - 100 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap
3.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
4.2: 18 h / 20 °C
5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
7.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 7 steps
1: copper(l) iodide; caesium carbonate; L-proline; sodium methansulfinate / dimethyl sulfoxide / 9 h / 95 - 100 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap
3: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
5: hydrogenchloride / water; 1,4-dioxane
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
7: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
(S)-2-((tert-butoxycarbonyl)amino)-3-((3-methylsulfonyl)phenyl)propanol
1289646-76-9

(S)-2-((tert-butoxycarbonyl)amino)-3-((3-methylsulfonyl)phenyl)propanol

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 0 °C
3: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
4: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
6: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap
2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
3.2: 18 h / 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
6.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 6 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap
2: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
4: hydrogenchloride / water; 1,4-dioxane
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
6: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 6 steps
1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 25 - 35 °C
1.2: 5 h / 25 - 45 °C
2.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h / 25 - 35 °C
3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 25 - 35 °C
3.2: 5 h / 25 - 45 °C
4.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 25 - 35 °C
5.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 25 - 35 °C
5.2: 5 h / 25 - 45 °C
6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 25 - 35 °C
View Scheme
(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-((3-methylsulfonyl)phenyl)propionate
1289646-78-1

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-((3-methylsulfonyl)phenyl)propionate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 0 °C
2: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
3: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
5: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
2.2: 18 h / 20 °C
3.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
5.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
3: hydrogenchloride / water; 1,4-dioxane
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
5: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
(2S)-2-amino-3-(3-(methanesulfonyl)phenyl)propionic acid benzyl ester hydrochloride
1194550-59-8

(2S)-2-amino-3-(3-(methanesulfonyl)phenyl)propionic acid benzyl ester hydrochloride

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
2: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
4: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
1.2: 18 h / 20 °C
2.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
4.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 4 steps
1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
2: hydrogenchloride / water; 1,4-dioxane
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
4: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
N-(2-chloroethyl)-3,5-dichlorobenzylamine hydrochloride
14046-52-7

N-(2-chloroethyl)-3,5-dichlorobenzylamine hydrochloride

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / 185 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 - 20 °C
3.2: -78 - 20 °C
4.1: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
5.1: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
7.1: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride; ammonium chloride / 185 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
4.2: 18 h / 20 °C
5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
7.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 9 steps
1: aluminum (III) chloride; ammonium chloride / 185 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
3: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
4: hydrogenchloride / 1,4-dioxane
5: sodium hydrogencarbonate
6: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
7: hydrogenchloride / water; 1,4-dioxane
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
9: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
C28H23Cl2N
1289646-72-5

C28H23Cl2N

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 - 20 °C
1.2: -78 - 20 °C
2.1: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
3.1: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
5.1: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
2.2: 18 h / 20 °C
3.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
5.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 7 steps
1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
2: hydrogenchloride / 1,4-dioxane
3: sodium hydrogencarbonate
4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
5: hydrogenchloride / water; 1,4-dioxane
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
7: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
5,7-dichloro-2-trityl-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
1194550-56-5

5,7-dichloro-2-trityl-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
2: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
4: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
1.2: 18 h / 20 °C
2.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
4.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 6 steps
1: hydrogenchloride / 1,4-dioxane
2: sodium hydrogencarbonate
3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
4: hydrogenchloride / water; 1,4-dioxane
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
6: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 3 steps
1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 20 h / 28 °C
2: sodium hydroxide / 1,4-dioxane; water / 2 h / 28 °C
3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 1.5 h / 10 - 20 °C
View Scheme
C46H40Cl2N2O5S
1194550-63-4

C46H40Cl2N2O5S

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
3: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
3: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / 1,4-dioxane; water / 2 h / 28 °C
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 1.5 h / 10 - 20 °C
View Scheme
benzyl (S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-[3-(methylsulfonyl)phenyl]propanoate hydrochloride
1194550-65-6

benzyl (S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-[3-(methylsulfonyl)phenyl]propanoate hydrochloride

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
2: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
3,5-dichlorobenzaldehyde
10203-08-4

3,5-dichlorobenzaldehyde

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: methanol; sodium cyanoborohydride / 20 °C
2.1: aluminum (III) chloride / 185 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C
4.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 - 20 °C
4.2: -78 - 20 °C
5.1: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
6.1: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
8.1: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: sodium cyanoborohydride
2: aluminum (III) chloride; ammonium chloride / 185 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
4: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
5: hydrogenchloride / 1,4-dioxane
6: sodium hydrogencarbonate
7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
8: hydrogenchloride / water; 1,4-dioxane
9: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
10: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 11 steps
1.1: ethanol / 2 h / 20 - 78 °C
2.1: sulfuric acid / dichloromethane / 7 h / 120 - 125 °C
2.2: 5 h / 0 - 50 °C / pH 12
3.1: platinum(IV) oxide / methanol / 0.17 h / 20 °C / Inert atmosphere
3.2: 25 h / 20 °C / 6464.52 Torr / Inert atmosphere
3.3: 0 - 40 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
5.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
6.1: hydrogenchloride / 1,4-dioxane
7.1: sodium hydrogencarbonate
8.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
9.1: hydrogenchloride / water; 1,4-dioxane
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
11.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 8 steps
1.1: sodium cyanoborohydride
2.1: aluminum (III) chloride; ammonium chloride / 185 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
4.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
5.2: 18 h / 20 °C
6.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
8.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 9 steps
1.1: ethanol / 2 h / 20 - 78 °C
2.1: sulfuric acid / dichloromethane / 7 h / 120 - 125 °C
2.2: 5 h / 0 - 50 °C / pH 12
3.1: platinum(IV) oxide / methanol / 0.17 h / 20 °C / Inert atmosphere
3.2: 25 h / 20 °C / 6464.52 Torr / Inert atmosphere
3.3: 0 - 40 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
5.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
6.2: 18 h / 20 °C
7.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
9.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
5,7-dichloro-1,2,3,4-tetrahydroisoquinoline
89315-56-0

5,7-dichloro-1,2,3,4-tetrahydroisoquinoline

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C
2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 - 20 °C
2.2: -78 - 20 °C
3.1: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
4.1: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
6.1: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
3.2: 18 h / 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
6.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 8 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
2: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
3: hydrogenchloride / 1,4-dioxane
4: sodium hydrogencarbonate
5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
6: hydrogenchloride / water; 1,4-dioxane
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
8: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
(S)-2-amino-3-(3-bromophenyl)propanoic acid
82311-69-1

(S)-2-amino-3-(3-bromophenyl)propanoic acid

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sodium hydrogencarbonate / 1,4-dioxane; water / 20 °C
2: copper(l) iodide; caesium carbonate; L-proline / dimethyl sulfoxide / 9 h / 100 °C
3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C
4: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 0 °C
5: triethylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
6: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
8: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran; methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium hydrogencarbonate / water; 1,4-dioxane
2.1: copper(l) iodide; caesium carbonate; L-proline; sodium methansulfinate / dimethyl sulfoxide / 9 h / 95 - 100 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap
4.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
5.2: 18 h / 20 °C
6.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
8.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 8 steps
1: sodium hydrogencarbonate / water; 1,4-dioxane
2: copper(l) iodide; caesium carbonate; L-proline; sodium methansulfinate / dimethyl sulfoxide / 9 h / 95 - 100 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap
4: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
6: hydrogenchloride / water; 1,4-dioxane
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
8: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
(3,5-dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine
1000210-73-0

(3,5-dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sulfuric acid / dichloromethane / 7 h / 120 - 125 °C
1.2: 5 h / 0 - 50 °C / pH 12
2.1: platinum(IV) oxide / methanol / 0.17 h / 20 °C / Inert atmosphere
2.2: 25 h / 20 °C / 6464.52 Torr / Inert atmosphere
2.3: 0 - 40 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
4.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
5.1: hydrogenchloride / 1,4-dioxane
6.1: sodium hydrogencarbonate
7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
8.1: hydrogenchloride / water; 1,4-dioxane
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
10.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 8 steps
1.1: sulfuric acid / dichloromethane / 7 h / 120 - 125 °C
1.2: 5 h / 0 - 50 °C / pH 12
2.1: platinum(IV) oxide / methanol / 0.17 h / 20 °C / Inert atmosphere
2.2: 25 h / 20 °C / 6464.52 Torr / Inert atmosphere
2.3: 0 - 40 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
4.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
5.2: 18 h / 20 °C
6.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
8.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
5,7-dichloro isoquinoline
73075-58-8

5,7-dichloro isoquinoline

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: platinum(IV) oxide / methanol / 0.17 h / 20 °C / Inert atmosphere
1.2: 25 h / 20 °C / 6464.52 Torr / Inert atmosphere
1.3: 0 - 40 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
4.2: 18 h / 20 °C
5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
7.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 9 steps
1.1: platinum(IV) oxide / methanol / 0.17 h / 20 °C / Inert atmosphere
1.2: 25 h / 20 °C / 6464.52 Torr / Inert atmosphere
1.3: 0 - 40 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
4.1: hydrogenchloride / 1,4-dioxane
5.1: sodium hydrogencarbonate
6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
7.1: hydrogenchloride / water; 1,4-dioxane
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
9.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
6-hydroxy-1,2,3,4-tetrahydroisoquinoline
14446-24-3

6-hydroxy-1,2,3,4-tetrahydroisoquinoline

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: N-chloro-succinimide / acetonitrile / 20 °C
2: sodium carbonate / methanol / 20 °C
3: pyridine / dichloromethane / 0.17 h / 0 - 2 °C
4: N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl-formamide / 20 °C / Reflux
5: sodium hydroxide / methanol / Reflux
6: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
7: hydrogenchloride / water; 1,4-dioxane
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
9: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
C15H16Cl2F3NO5S
851784-78-6

C15H16Cl2F3NO5S

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl-formamide / 20 °C / Reflux
2: sodium hydroxide / methanol / Reflux
3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
4: hydrogenchloride / water; 1,4-dioxane
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
6: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
2-(tert-butyl) 6-methyl 5,7-dichloro-3,4-dihydroisoquinoline-2,6(1Η)-dicarboxylate
851784-80-0

2-(tert-butyl) 6-methyl 5,7-dichloro-3,4-dihydroisoquinoline-2,6(1Η)-dicarboxylate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydroxide / methanol / Reflux
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
3: hydrogenchloride / water; 1,4-dioxane
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
5: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol / 20 °C
2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium hydroxide; water / methanol / 20 °C
2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / -10 - 20 °C
View Scheme
2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
851784-82-2

2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
2: hydrogenchloride / water; 1,4-dioxane
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
4: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C
2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / -10 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 25 - 35 °C
1.2: 2 h / 25 - 35 °C
2.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / tetrahydrofuran / 0.5 h / 25 - 35 °C
2.2: 3 h / 25 - 35 °C
3.1: pyridine; lithium iodide hydrate / 100 - 105 °C
4.1: triethylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 25 - 35 °C
4.2: 2 h / 25 - 35 °C
View Scheme
C9H9Cl2NO*C7H8O3S
1609545-55-2

C9H9Cl2NO*C7H8O3S

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sodium carbonate / methanol / 20 °C
2: pyridine / dichloromethane / 0.17 h / 0 - 2 °C
3: N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl-formamide / 20 °C / Reflux
4: sodium hydroxide / methanol / Reflux
5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
6: hydrogenchloride / water; 1,4-dioxane
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
8: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
tert-butyl 5,7-dichloro-6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
851784-76-4

tert-butyl 5,7-dichloro-6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: pyridine / dichloromethane / 0.17 h / 0 - 2 °C
2: N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl-formamide / 20 °C / Reflux
3: sodium hydroxide / methanol / Reflux
4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
5: hydrogenchloride / water; 1,4-dioxane
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
7: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 5 steps
1: pyridine / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; N-ethyl-N,N-diisopropylamine; palladium diacetate / N,N-dimethyl acetamide / 20 °C
3: lithium hydroxide; water / methanol / 20 °C
4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 5 °C
View Scheme
Multi-step reaction with 5 steps
1: pyridine / -20 - 20 °C
2: 1,3-bis-(diphenylphosphino)propane; N-ethyl-N,N-diisopropylamine; palladium diacetate / N,N-dimethyl acetamide / 20 °C
3: lithium hydroxide; water / methanol / 20 °C
4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C
5: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / -10 - 20 °C
View Scheme
benzyl (S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-[3-(methylsulfonyl)phenyl]propanoate hydrochloride
1194550-65-6

benzyl (S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-[3-(methylsulfonyl)phenyl]propanoate hydrochloride

benzofuran-6-carboxylic chloride

benzofuran-6-carboxylic chloride

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
2: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
6-hydroxybenzofuran-3-one
6272-26-0

6-hydroxybenzofuran-3-one

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: triethylamine / acetone
2: sodium tetrahydroborate / methanol / 20 °C
3: hydrogenchloride; water / tetrahydrofuran / 28 °C / Inert atmosphere; Darkness
4: dichloromethane / 72 h
5: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 6 h / 70 °C / 6000.6 Torr / Autoclave
6: lithium hydroxide; water / methanol
7: oxalyl dichloride / N,N-dimethyl-formamide / 5.5 h
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
9: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
5,7-dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride
73075-47-5

5,7-dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.17 h
3.2: 18 h / 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
6.1: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 8 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 25 °C
2: n-butyllithium; N,N,N,N,-tetramethylethylenediamine
3: hydrogenchloride / 1,4-dioxane
4: sodium hydrogencarbonate
5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide
6: hydrogenchloride / water; 1,4-dioxane
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 5 °C
8: triethylamine; palladium 10% on activated carbon; formic acid / tetrahydrofuran; methanol
View Scheme
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

lifitegrast dicyclohexylamine salt

lifitegrast dicyclohexylamine salt

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h;70%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

1-isobutyric acid chloromethyl ester
84674-32-8

1-isobutyric acid chloromethyl ester

1-(isobutyryloxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

1-(isobutyryloxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 16h; Sealed tube;61%
1-Chloroethyl methyl carbonate
80196-03-8

1-Chloroethyl methyl carbonate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

1-((methoxycarbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

1-((methoxycarbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 50℃; for 38h;42%
1-chloroethyl acetate
5912-58-3

1-chloroethyl acetate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

1-acetoxyethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

1-acetoxyethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 16h; Sealed tube;39%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

methyl (2R)-2-(((1-chloroethoxy)carbonyl)oxy)propanoate

methyl (2R)-2-(((1-chloroethoxy)carbonyl)oxy)propanoate

1-(((((R)-1-methoxy-1-oxopropan-2-yl)oxy)carbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

1-(((((R)-1-methoxy-1-oxopropan-2-yl)oxy)carbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 16h; Sealed tube;37%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

2-((((1-chloroethoxy)carbonyl)oxy)methyl)propane-1,3-diyl bis(2,2-dimethylpropanoate)

2-((((1-chloroethoxy)carbonyl)oxy)methyl)propane-1,3-diyl bis(2,2-dimethylpropanoate)

2-((8S)-10-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)-5-methyl-8-(3-(methylsulfonyl)benzyl)-3,7,10-trioxo-2,4,6-trioxa-9-azadecyl)propane-1,3-diyl bis(2,2-dimethylpropanoate)

2-((8S)-10-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)-5-methyl-8-(3-(methylsulfonyl)benzyl)-3,7,10-trioxo-2,4,6-trioxa-9-azadecyl)propane-1,3-diyl bis(2,2-dimethylpropanoate)

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; Sealed tube;36%
propanoic acid,1-chloroethyl ester
58304-44-2

propanoic acid,1-chloroethyl ester

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

C34H32Cl2N2O9S

C34H32Cl2N2O9S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 18h; Inert atmosphere;35%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

2-((((1-chloroethoxy)carbonyl)oxy)methyl)propane-1,3-diyl diacetate

2-((((1-chloroethoxy)carbonyl)oxy)methyl)propane-1,3-diyl diacetate

2-((8S)-10-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)-5-methyl-8-(3-(methylsulfonyl)benzyl)-3,7,10-trioxo-2,4,6-trioxa-9-azadecyl)propane-1,3-diyl diacetate

2-((8S)-10-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)-5-methyl-8-(3-(methylsulfonyl)benzyl)-3,7,10-trioxo-2,4,6-trioxa-9-azadecyl)propane-1,3-diyl diacetate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 72h;34%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

1-(isopropoxycarbonyloxy)ethyl chloride
98298-66-9

1-(isopropoxycarbonyloxy)ethyl chloride

1-((isopropoxycarbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

1-((isopropoxycarbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 2h;24%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

1-chloroethyl pivalate
40258-80-8

1-chloroethyl pivalate

1-(((S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoyl)oxy)ethyl pivalate

1-(((S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoyl)oxy)ethyl pivalate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 72h; Inert atmosphere;22%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

1-chloroethyl 5-((R)-1,2-dithiolan-3-yl)pentanoate

1-chloroethyl 5-((R)-1,2-dithiolan-3-yl)pentanoate

1-(((S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoyl)oxy)ethyl 5-((R)-1,2-dithiolan-3-yl)pentanoate

1-(((S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoyl)oxy)ethyl 5-((R)-1,2-dithiolan-3-yl)pentanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 16h;4%
(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
1025967-78-5

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

1-Chloroethyl ethyl carbonate
50893-36-2

1-Chloroethyl ethyl carbonate

1-((ethoxycarbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

1-((ethoxycarbonyl)oxy)ethyl (2S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 20h; Inert atmosphere;3%

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