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Hangzhou Maytime Bio-Tech Co.,Ltd.

High quality .Competitive price. Application:Ledipasvir intermediate Port:any Chinese port

High quality Ledipasvir intermediate CAS:1256387-74-2

Cas:1256387-74-2

Min.Order:0 Metric Ton

Negotiable

Type:Other

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's 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. DayangChem can provide different quantities

(1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Cas:1256387-74-2

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Hangzhou Think Chemical Co. Ltd

(1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester CAS No.:1256387-74-2 Name: (1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]hepta

Henan Allgreen Chemical Co.,Ltd

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- Basic information Product Name: 2-Azabicyclo[2.2.1]heptane-2-carboxylic aci

Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new api, intermedi

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

(1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Cas:1256387-74-2

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Jinan Finer Chemical Co., Ltd

Product Description Product website: http://www.finerchem.com/pro01en/id/945.html Product Name (1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic aci

(1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Cas:1256387-74-2

Min.Order:1 Gram

FOB Price: $66.0

Type:Lab/Research institutions

inquiry

LIDE PHARMACEUTICALS LIMITED

LIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc.

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-

Cas:1256387-74-2

Min.Order:1 Kilogram

FOB Price: $0.9 / 1.0

Type:Lab/Research institutions

inquiry

Henan Tianfu Chemical Co., Ltd.

Competitive Price High Quality Fast Delivery custom-made Welcome to Henan Tianfu Chemical Co., Ltd. website. Our company engages in Sodium Tripolyphosphate (STPP) and Sodium Hexametabphosphate (SHMP) production; development of noble me

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

HPLC 98%CAS 1256387-74-2 with high quality products

Cas:1256387-74-2

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Name: (1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester Synonyms: 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- C

Hubei Langyou International Trading Co., Ltd

Advantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best service is

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

Ledipasvir Intermediate CAS 1256387-74-2

Cas:1256387-74-2

Min.Order:100 Kilogram

FOB Price: $1.0 / 5.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- CAS:1256387-74-2 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and dev

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

SICHUAN TONGSHENG AMINOACID CO.LTD

Product name: (1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester CAS number: 1256387-74-2 molecular formula: C18H22BrN3O2 Assay: MI

Triumph International Development Limilted

Triumph has the complete production of G- KG - MT service chain,we can make the new technology into productivity quickly in the research and development of new products. Main Service 1.Own made fine chemical products 2.Out sourcing and qua

(1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Cas:1256387-74-2

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

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

Shanghai SE Pharm Co., Ltd

1. made in GMP plant, commerially 2. usually have it in stock 3. can supply at large quantity 4. audit accepted. related documents are available to offer and audited by many clients, such as lupin, msn, dr reddy etc 5. chromatographic p

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

Chemlyte Solutions

Chemlyte Solutions believe that customers and suppliers deserve much more than what traditional distributors can offer. To grow in today s fast-paced and increasingly competitive market it is essential to be able to quickly adapt to market forces eff

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

Hangzhou Lingrui Chemical Co.,Ltd.

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-Appearance:White powder Storage:Store in well-closed container, protected from light and in cool & dry place. Package:according to cus

Siwei Development Group Ltd.

Product name: (1R,3S,4S)-3-(6-Bromo-1H-Benzimidazol-2-yl)-2-Azabicyclo[2,2,1]Heptane-2-Carboxylic Acid 1,1-Dimethylethyl Ester CAS No.:1256387-74-2 Molecule Formula:CC18H22BrN3O2 Molecule Weight:392.29 Purity: 99.0% Package: 25kg/drum Descripti

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,

(1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2...

Cas:1256387-74-2

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,

Shanghai Minstar Chemical Co., Ltd

Product Name: 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- Synonyms: 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl este

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology 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 chemicals. W

Hangzhou Zhongqi chem Co.,Ltd.

Located in Hangzhou National Hi-Tech Industrial Development Zone, zhongqichem is a technical company mainly focus on the Custom synthesis, manufacturing, sales of chemicals to various industries. Benefiting from the outstanding customer service an

Synthetic route

C18H24BrN3O3

C18H24BrN3O3

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With acetic acid In tert-butyl methyl ether at 70℃; Reagent/catalyst; Solvent; Temperature;96.8%
With acetic acid In acetonitrile at 80℃; for 12h; Solvent;87%
4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

(1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester

(1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: 4-Bromo-benzene-1,2-diamine; (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl acetamide at 10 - 20℃; for 20h; Cooling with ice;
Stage #2: With acetic acid In tert-butyl methyl ether at 55℃; for 18h;
94%
Stage #1: 4-Bromo-benzene-1,2-diamine; (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester With 4-methyl-morpholine; 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 20℃; for 1h;
Stage #2: In ethanol at 115℃; for 48h;
1.59 g
(1R,3S,4S)-2-tert-butoxycarbonyl-3-(2-amino-4-bromophenylaminocarbonyl)-2-azabicyclo[2.2.1]heptane
1256387-73-1

(1R,3S,4S)-2-tert-butoxycarbonyl-3-(2-amino-4-bromophenylaminocarbonyl)-2-azabicyclo[2.2.1]heptane

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With ethanol at 130 - 170℃; for 72h; Sealed tube;72%
In ethanol at 130 - 170℃; Sealed tube;72%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(1R,3S,4S)-2-tert-butoxycarbonyl-3-(2-amino-4-bromophenylaminocarbonyl)-2-azabicyclo[2.2.1]heptane
1256387-73-1

(1R,3S,4S)-2-tert-butoxycarbonyl-3-(2-amino-4-bromophenylaminocarbonyl)-2-azabicyclo[2.2.1]heptane

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: 3-(2-amino-4-bromo-phenylcarbamoyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester In ethanol at 130 - 170℃; Sealed tube;
Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃;
72%
C18H24BrN3O3
1256387-73-1

C18H24BrN3O3

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With acetic acid at 50 - 60℃; for 3h;
(1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester

(1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: ethanol / 130 - 170 °C / Sealed tube
2.2: 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
2: ethanol / 130 - 170 °C / Sealed tube
View Scheme
Multi-step reaction with 3 steps
1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
2: iron(III) chloride hexahydrate; hydrazine hydrate; pyrographite / toluene; ethanol / 5 h / 60 - 65 °C
3: acetic acid / acetonitrile / 12 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: pivaloyl chloride / -10 - -5 °C
2: pyridinium hydrobromide perbromide / N,N-dimethyl-formamide / 0 °C
3: acetic acid / tert-butyl methyl ether / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
2: ethanol / 72 h / 130 - 170 °C / Sealed tube
View Scheme
4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: ethanol / 130 - 170 °C / Sealed tube
2.2: 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
2: ethanol / 72 h / 130 - 170 °C / Sealed tube
View Scheme
(1R,3S,4S)-methyl 2-((R)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

(1R,3S,4S)-methyl 2-((R)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: palladium on carbon; hydrogen / ethanol; methanol / 15 h / 30 - 35 °C / 5171.62 Torr
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.5 h / 8 - 20 °C
3: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h
4: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
5: ethanol / 130 - 170 °C / Sealed tube
View Scheme
(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid methyl ester

(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid methyl ester

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.5 h / 8 - 20 °C
2: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h
3: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
4: ethanol / 130 - 170 °C / Sealed tube
View Scheme
(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester
1181573-36-3

(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h
2: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
3: ethanol / 130 - 170 °C / Sealed tube
View Scheme
5-bromo-2-nitroaniline
5228-61-5

5-bromo-2-nitroaniline

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
2: iron(III) chloride hexahydrate; hydrazine hydrate; pyrographite / toluene; ethanol / 5 h / 60 - 65 °C
3: acetic acid / acetonitrile / 12 h / 80 °C
View Scheme
C18H22BrN3O5

C18H22BrN3O5

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron(III) chloride hexahydrate; hydrazine hydrate; pyrographite / toluene; ethanol / 5 h / 60 - 65 °C
2: acetic acid / acetonitrile / 12 h / 80 °C
View Scheme
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pivaloyl chloride / -10 - -5 °C
2: pyridinium hydrobromide perbromide / N,N-dimethyl-formamide / 0 °C
3: acetic acid / tert-butyl methyl ether / 70 °C
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

2-chloro-1-(9,9-difluoro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl)ethanone

2-chloro-1-(9,9-difluoro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl)ethanone

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-chloroacetyl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-chloroacetyl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
Stage #1: 2-chloro-1-(9,9-difluoro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl)ethanone With potassium carbonate In Dimethyl ether; water at 20℃; for 0.166667h;
Stage #2: (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0) In Dimethyl ether; water at 90 - 95℃; Suzuki Coupling;
96%
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-87-7

(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 90℃;94%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; for 3.5h; Inert atmosphere;1.16 g
With bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride; potassium carbonate In 1,2-dimethoxyethane Reflux; Inert atmosphere;
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

benzene-1,4-diboronic acid bispinacol ester
99770-93-1

benzene-1,4-diboronic acid bispinacol ester

(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-87-7

(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 4h; Inert atmosphere;85%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 4h; Inert atmosphere;85%
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

benzene-1,4-diboronic acid bispinacol ester
99770-93-1

benzene-1,4-diboronic acid bispinacol ester

(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
1256387-75-3

(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 4h; Suzuki Coupling; Inert atmosphere;85%
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

(6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester

(6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester

oxalic acid
144-62-7

oxalic acid

C2H2O4*C45H48F2N6O4

C2H2O4*C45H48F2N6O4

Conditions
ConditionsYield
Stage #1: (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester With bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride; potassium propionate; bis(pinacol)diborane In Isopropyl acetate at 75℃; for 3.5h;
Stage #2: (6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester With potassium phosphate In Isopropyl acetate at 75℃; for 1h;
Stage #3: oxalic acid Further stages;
81%
(S)-tert-butyl 2-(4-(6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-lH-imidazol-2-yl)pyrrolidine-1-carboxylate
1228552-26-8

(S)-tert-butyl 2-(4-(6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-lH-imidazol-2-yl)pyrrolidine-1-carboxylate

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

C40H46N6O4
1273592-32-7

C40H46N6O4

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 98℃; for 5h; Inert atmosphere;62%
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

C30H38BN3O4
1273592-38-3

C30H38BN3O4

(1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
1256387-76-4

(1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 98℃; for 2.5h; Inert atmosphere;45%
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

C23H31N3O2Si
1273592-35-0

C23H31N3O2Si

Conditions
ConditionsYield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 85℃; Inert atmosphere;
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

C20H23N3O2
1273592-36-1

C20H23N3O2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / acetonitrile / 85 °C / Inert atmosphere
2: potassium carbonate; methanol / 1.5 h / 20 °C
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

C38H44N6O4
1273592-22-5

C38H44N6O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / acetonitrile / 85 °C / Inert atmosphere
2: potassium carbonate; methanol / 1.5 h / 20 °C
3: triethylamine / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / acetonitrile / 15 h / 35 °C / Inert atmosphere
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

3-[6-(9,9-difluoro-7-{2-[5-(2-methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-9H-fluoren-2-yl)-1H-benzoimidazol-2-yl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
1256393-27-7

3-[6-(9,9-difluoro-7-{2-[5-(2-methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-9H-fluoren-2-yl)-1H-benzoimidazol-2-yl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere
2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 5 h / 85 - 90 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere
2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 5 h / 85 - 90 °C / Inert atmosphere
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

(1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
1256387-76-4

(1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 4 h / 90 °C / Inert atmosphere
2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 90 °C / Inert atmosphere
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
1256388-06-3

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C
2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 3 h / 90 °C / Inert atmosphere
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-((S)-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptan-6-yl)-1H-imidazol-5-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-((S)-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptan-6-yl)-1H-imidazol-5-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C
2: sodium hydrogencarbonate; palladium diacetate; triphenylphosphine / water; 1,2-dimethoxyethane / 4 h / 93 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 3.5 h / 95 °C / Inert atmosphere
2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / 4 h / 93 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride; potassium acetate / 1,4-dioxane / 80 - 85 °C
2: sodium carbonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water; N,N-dimethyl-formamide / 80 - 85 °C / Inert atmosphere
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

C45H48F2N6O4*ClH

C45H48F2N6O4*ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C
2: sodium hydrogencarbonate; palladium diacetate; triphenylphosphine / water; 1,2-dimethoxyethane / 4 h / 93 °C / Inert atmosphere
3: hydrogenchloride / 1,4-dioxane; dichloromethane / 0.33 h / 20 °C
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

methyl (S)-1-((S)-2-(5-(4'-(2-((1R,3S,4S)-2-((S)-2-(acetoxyamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)biphenyl-4-yl)-1Himidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate
1256387-78-6

methyl (S)-1-((S)-2-(5-(4'-(2-((1R,3S,4S)-2-((S)-2-(acetoxyamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)biphenyl-4-yl)-1Himidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 4 h / 90 °C / Inert atmosphere
2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 90 °C / Inert atmosphere
3.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h / 20 °C
3.2: 0.83 h / 0 °C
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

methyl (S)-1-((S)-2-(5-(7-(2-((1R,3S,4S)-2-((S)-2-(acetoxyamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate
1256388-07-4

methyl (S)-1-((S)-2-(5-(7-(2-((1R,3S,4S)-2-((S)-2-(acetoxyamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C
2.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 3 h / 90 °C / Inert atmosphere
3.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C
3.2: 0.5 h / 0 °C
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

methyl [(2S)-1-{(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate
1256388-51-8

methyl [(2S)-1-{(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C
2: sodium hydrogencarbonate; palladium diacetate; triphenylphosphine / water; 1,2-dimethoxyethane / 4 h / 93 °C / Inert atmosphere
3: hydrogenchloride / 1,4-dioxane; dichloromethane / 0.33 h / 20 °C
4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium propionate; bis(pinacol)diborane / Isopropyl acetate / 3 h / 75 °C / Inert atmosphere
1.2: 15 h / 75 °C / Inert atmosphere
2.1: hydrogenchloride / acetonitrile; water / 6 h / 65 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 0 °C
3.2: 4 h / 25 °C
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / acetonitrile / 3 h / 60 - 65 °C
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide; ethyl acetate / 16 h / 0 - 30 °C
3: potassium propionate / Isopropyl acetate / 69 - 72 °C / Inert atmosphere
4: potassium phosphate / Isopropyl acetate; water / 2 h / 65 - 72 °C
5: ammonium acetate / toluene; 2-methoxy-ethanol / 5 h / 100 - 102 °C
View Scheme
Multi-step reaction with 4 steps
1.1: bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride; potassium acetate / 1,4-dioxane / 80 - 85 °C
2.1: sodium carbonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water; N,N-dimethyl-formamide / 80 - 85 °C / Inert atmosphere
3.1: hydrogenchloride / 1,4-dioxane; water / 70 - 75 °C
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.33 h / 23 °C
4.2: 4 h / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium propionate; bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride; Isopropyl acetate / 3 h / 70 °C / Inert atmosphere
2.1: aq. phosphate buffer / 0.5 h / 70 °C / Inert atmosphere
2.2: 0.5 h / 35 °C / Inert atmosphere
2.3: 9 h / 55 °C
3.1: hydrogenchloride / water; acetonitrile / 1.5 h / 60 °C
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C / Autoclave
4.2: 3.5 h / 0 - 20 °C / Autoclave
View Scheme
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

(6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester

(6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-((S)-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptan-6-yl)-1H-imidazol-5-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

(1R,3S,4S)-tert-butyl 3-(6-(7-(2-((S)-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptan-6-yl)-1H-imidazol-5-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester With potassium propionate; bis(pinacol)diborane In Isopropyl acetate at 75℃; for 3h; Inert atmosphere;
Stage #2: (6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester With palladium diacetate; sodium hydrogencarbonate; triphenylphosphine In acetonitrile at 75℃; for 15h; Inert atmosphere;
50 g

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