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Sinoway Industrial Co., Ltd.

1. Usage of OMarigliptin (MK-3102) Psychotherapeutic, Hypoglycemic agents 2. Sinoway's advantage: (1) ISO 9001:2008 certificated company (2) 28 years in pharmaceutical industry (3)China office of Fischer Chemicals AG (Switze

Supply High Quality OMarigliptin (MK-3102) CAS No. 1226781-44-7

Cas:1226781-44-7

Min.Order:1 Gram

FOB Price: $40.0

Type:Trading Company

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Hangzhou Think Chemical Co. Ltd

Omarigliptin CAS No.:1226781-44-7 Name: (2R,3S,5R)-2-(2,5-Difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine Molecular Structure

High purity Omarigliptin CAS No.:1226781-44-7

Cas:1226781-44-7

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% Omarigliptin (MK-3102) 1226781-44-7 GMP Manufacturer

Cas:1226781-44-7

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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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 ap

Omarigliptin (MK-3102)

Cas:1226781-44-7

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

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Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product s

Omarigliptin Manufacturer/High quality/Best price/In stock

Cas:1226781-44-7

Min.Order:1 Kilogram

FOB Price: $6.0

Type:Lab/Research institutions

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Hebei yanxi chemical co.,LTD.

hebei yanxi chemical co., LTD who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do research and developm

Omarigliptin Manufacturer/High quality/Best price/In stock CAS NO.1226781-44-7

Cas:1226781-44-7

Min.Order:1 Metric Ton

FOB Price: $1.0 / 3.0

Type:Trading Company

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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

MK-3102

Cas:1226781-44-7

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

MK-3102 Basic information Product Name: MK-3102 Synonyms: MK-3102;(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(Methylsulfonyl)pyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)tetrahydro-2H-pyran-3-aMine;

MK-3102

Cas:1226781-44-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

Omarigliptin (MK-3102)

Cas:1226781-44-7

Min.Order:1 Gram

FOB Price: $1000.0 / 1300.0

Type:Trading Company

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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

Pharmaceutical Grade CAS 1226781-44-7 with competitive price

Cas:1226781-44-7

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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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 serv

Omarigliptin (MK-3102) Manufacturer For Hypoglycemic Agents

Cas:1226781-44-7

Min.Order:10 Gram

Negotiable

Type:Other

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Shanghai Upbio Tech Co.,Ltd

1.In No Less 10 years exporting experience. you can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specializ

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

Omarigliptin 99%

Cas:1226781-44-7

Min.Order:1 Kilogram

FOB Price: $41.0 / 56.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

Omarigliptin (MK-3102) CAS:1226781-44-7 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

Omarigliptin (MK-3102) CAS:1226781-44-7

Cas:1226781-44-7

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

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need C

Omarigliptin manufacturer with low price

Cas:1226781-44-7

Min.Order:1 Gram

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

Triumph International Development Limilted

Appearance:white powder/crystal Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:Common products:Sea/A

Omarigliptin

Cas:1226781-44-7

Min.Order:100 Metric Ton

Negotiable

Type:Lab/Research institutions

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Nanjing Fred Technology Co.,Ltd.

Omarigliptin (MK-3102) is one of the most competitive products in our company, we can supply it with good quality and best price. Appearance:solid Storage:Room temperature, Keep in Dark Place. Package:According to the demand of customer Application:A

Omarigliptin (MK-3102)

Cas:1226781-44-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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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-

MK-3102 Omarigliptin 1226781-44-7

Cas:1226781-44-7

Min.Order:1 Gram

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

Omarigliptin Manufacturer/High quality/Best price/In stock CAS NO.1226781-44-7

Cas:1226781-44-7

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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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

OMARIGLIPTIN

Cas:1226781-44-7

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

ACHIEVER SYSTEAM BIOCHEM CO., LTD.

We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to provide excellence in researching, manufacturing and drug discovery process. Our research team of scienti

MK3102

Cas:1226781-44-7

Min.Order:10 Gram

FOB Price: $1.0

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

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

Omarigliptin (MK-3102)

Cas:1226781-44-7

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

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

MK-3102

Cas:1226781-44-7

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

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TaiChem Taizhou Limited

Established in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site

Omarigliptin (MK-3102)

Cas:1226781-44-7

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

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Siwei Development Group Ltd.

Product name: Omarigliptin CAS No.:1226781-44-7 Molecule Formula:C17H20F2N4O3S Molecule Weight:398.43 Purity: 99.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTING ITEMS

Best Quality Omarigliptin with good supplier

Cas:1226781-44-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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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,

Omarigliptin (MK-3102)

Cas:1226781-44-7

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Jiangsu Qianyu Molecular Technology Co., LTD.

Our Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an

Best PriceOmarigliptin (MK-3102)

Cas:1226781-44-7

Min.Order:0

Negotiable

Type:Trading Company

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Synthetic route

C17H18F2N4O5S

C17H18F2N4O5S

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
With acetic acid; zinc In butan-1-ol at 30℃; Temperature; Solvent;100%
tert-butyl ((2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)tetrahydro-2H-pyran-3-yl)carbamate
1226781-87-8

tert-butyl ((2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)tetrahydro-2H-pyran-3-yl)carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Stage #1: tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate With sulfuric acid In N,N-dimethyl acetamide; water at 20℃; for 18.5h;
Stage #2: With ammonium hydroxide In N,N-dimethyl acetamide; water pH=10.2;
89%
With trifluoroacetic acid In dichloromethane at 0 - 35℃; for 0.5h;84%
With sulfuric acid In N,N-dimethyl acetamide; water Reagent/catalyst; Solvent;74.3%
C18H20F2N4O4S

C18H20F2N4O4S

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide; zinc(II) chloride In water at 0 - 60℃; for 6h; Large scale;87.1%
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
951127-25-6

N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester

tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate
1226781-82-3

tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate With trifluoroacetic acid at 0 - 2℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride; triethylamine In N,N-dimethyl acetamide at 0 - 2℃; for 5h;
63%
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
951127-25-6

N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester

2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate
1280210-80-1

2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate With trifluoroacetic acid at 0 - 2℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride; triethylamine In N,N-dimethyl acetamide at 0 - 2℃; for 5h;
57%
Multi-step reaction with 2 steps
1.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
2.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
2.2: pH 10.2
View Scheme
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
2: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 7.67 h / 0 - 20 °C / Large scale
2: benzenesulfonic acid; potassium fluoride / water; dichloromethane / 20 °C / Inert atmosphere; Large scale
View Scheme
2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate
1280210-80-1

2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl acetamide; sodium tris(acetoxy)borohydride / 0.67 h / 0 - 20 °C
2: benzenesulfonic acid / dichloromethane / 20 °C / Inert atmosphere
View Scheme
tert-butyl {(2R.3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate

tert-butyl {(2R.3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
With benzenesulfonic acid In dichloromethane at 20℃; Inert atmosphere;
[(2R,3S)-5-methylene-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamic acid tert-butyl ester
951127-31-4

[(2R,3S)-5-methylene-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamic acid tert-butyl ester

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
2.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
3.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
3.2: pH 10.2
View Scheme
tert-butyl (3Z)-3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate
905274-02-4

tert-butyl (3Z)-3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: hydrazine / ethanol / 4 h / 85 °C / Sealed tube
2.1: hydrogenchloride / water / 6 h
3.1: ammonia / methanol; water
4.1: triethylamine / dichloromethane / 20 °C
5.1: sodium hydride / acetonitrile; mineral oil / 2 h / 20 °C / Inert atmosphere
5.2: 1 h / 20 °C / Inert atmosphere
5.3: 18 h / 20 - 30 °C
6.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
7.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
7.2: pH 10.2
View Scheme
1,4,5,6-tetrahydropyrrolo[3, 4-c]pyrazole
6573-19-9, 769895-06-9

1,4,5,6-tetrahydropyrrolo[3, 4-c]pyrazole

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 20 °C
2.1: sodium hydride / acetonitrile; mineral oil / 2 h / 20 °C / Inert atmosphere
2.2: 1 h / 20 °C / Inert atmosphere
2.3: 18 h / 20 - 30 °C
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
4.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
4.2: pH 10.2
View Scheme
4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester
657428-42-7

4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / acetonitrile; mineral oil / 2 h / 20 °C / Inert atmosphere
1.2: 1 h / 20 °C / Inert atmosphere
1.3: 18 h / 20 - 30 °C
2.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
3.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
3.2: pH 10.2
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / acetonitrile / Inert atmosphere
1.2: Inert atmosphere
2.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
3.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / 2-methyltetrahydrofuran / -5 °C / Inert atmosphere
1.2: 1 h / -5 °C / Inert atmosphere
2.1: Isopropyl acetate / 22 °C / Inert atmosphere
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
4.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: sodium hydride / acetonitrile / Inert atmosphere
2: Isopropyl acetate / 22 °C / Inert atmosphere
3: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
4: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine; potassium tert-butylate / 2-methyltetrahydrofuran / 3 h / -10 - 20 °C / Inert atmosphere; Large scale
1.2: 2 h / 20 °C / Inert atmosphere; Large scale
2.1: Isopropyl acetate / 0 - 20 °C / Large scale
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 7.67 h / 0 - 20 °C / Large scale
4.1: benzenesulfonic acid; potassium fluoride / water; dichloromethane / 20 °C / Inert atmosphere; Large scale
View Scheme
C12H13F2NO

C12H13F2NO

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dichloromethane / 20 h / 20 °C
2.1: Chiralpak IA / Resolution of racemate
3.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
5.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
5.2: pH 10.2
View Scheme
C17H21F2NO3

C17H21F2NO3

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Chiralpak IA / Resolution of racemate
2.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
4.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
4.2: pH 10.2
View Scheme
C12H22N4O2

C12H22N4O2

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride / water / 6 h
2.1: ammonia / methanol; water
3.1: triethylamine / dichloromethane / 20 °C
4.1: sodium hydride / acetonitrile; mineral oil / 2 h / 20 °C / Inert atmosphere
4.2: 1 h / 20 °C / Inert atmosphere
4.3: 18 h / 20 - 30 °C
5.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
6.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
6.2: pH 10.2
View Scheme
C7H14N4*ClH

C7H14N4*ClH

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ammonia / methanol; water
2.1: triethylamine / dichloromethane / 20 °C
3.1: sodium hydride / acetonitrile; mineral oil / 2 h / 20 °C / Inert atmosphere
3.2: 1 h / 20 °C / Inert atmosphere
3.3: 18 h / 20 - 30 °C
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
5.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
5.2: pH 10.2
View Scheme
2,5-difluorobenzaldehyde
2646-90-4

2,5-difluorobenzaldehyde

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol / 1 h / 5 °C
2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 10 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 2 h / 20 °C
5.1: zinc; acetic acid / ethanol / 1 h
6.1: dichloromethane / 20 h / 20 °C
7.1: Chiralpak IA / Resolution of racemate
8.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
9.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
10.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
10.2: pH 10.2
View Scheme
Multi-step reaction with 5 steps
1.1: sodium t-butanolate; C38H48N4P(1+)*Cl(1-) / toluene / 0.5 h / 20 °C / Inert atmosphere
2.1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; [RhCl(P(3-F-Ph)3)2] / N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere
3.1: pyridine / methanol / 0.5 h / -30 °C / Inert atmosphere
3.2: -20 °C
3.3: 1 h / 20 °C
4.1: lithium borohydride / N,N-dimethyl-formamide / 1 h / -15 °C / Inert atmosphere; Large scale
5.1: zinc; acetic acid / butan-1-ol / 30 °C
View Scheme
1-(2,5-difluorophenyl)-2-nitroethanol
951127-26-7

1-(2,5-difluorophenyl)-2-nitroethanol

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: Dess-Martin periodane / dichloromethane / 2.5 h / 10 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
3.1: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 2 h / 20 °C
4.1: zinc; acetic acid / ethanol / 1 h
5.1: dichloromethane / 20 h / 20 °C
6.1: Chiralpak IA / Resolution of racemate
7.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
8.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
9.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
9.2: pH 10.2
View Scheme
1-(2,5-difluorophenyl)-2-nitroethanone
951127-27-8

1-(2,5-difluorophenyl)-2-nitroethanone

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
2.1: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 2 h / 20 °C
3.1: zinc; acetic acid / ethanol / 1 h
4.1: dichloromethane / 20 h / 20 °C
5.1: Chiralpak IA / Resolution of racemate
6.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
7.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
8.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
8.2: pH 10.2
View Scheme
6-(2,5-difluorophenyl)-3-methylidene-5-nitro-3,4-dihydro-2H-pyran
951127-28-9

6-(2,5-difluorophenyl)-3-methylidene-5-nitro-3,4-dihydro-2H-pyran

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 2 h / 20 °C
2.1: zinc; acetic acid / ethanol / 1 h
3.1: dichloromethane / 20 h / 20 °C
4.1: Chiralpak IA / Resolution of racemate
5.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
6.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
7.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
7.2: pH 10.2
View Scheme
trans-5-methylene-3-nitro-2-(2,5-difluorophenyl)-tetrahydro-2H-pyran

trans-5-methylene-3-nitro-2-(2,5-difluorophenyl)-tetrahydro-2H-pyran

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: zinc; acetic acid / ethanol / 1 h
2.1: dichloromethane / 20 h / 20 °C
3.1: Chiralpak IA / Resolution of racemate
4.1: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C
5.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 2 h / -10 °C
6.1: sulfuric acid / water; N,N-dimethyl acetamide / 18.5 h / 20 °C
6.2: pH 10.2
View Scheme
tert-butyl [(1S,2S)-1-(2,5-difluorophenyl)-1-hydroxypent-4-yn-2-yl]carbamate

tert-butyl [(1S,2S)-1-(2,5-difluorophenyl)-1-hydroxypent-4-yn-2-yl]carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1-hydroxy-pyrrolidine-2,5-dione; tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate / N,N-dimethyl-formamide / Inert atmosphere; Large scale
1.2: 75 - 85 °C / Inert atmosphere; Large scale
2.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Large scale
2.2: 0 - 20 °C / Large scale
3.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 15 h / 0 - 20 °C / Inert atmosphere; Large scale
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 7.67 h / 0 - 20 °C / Large scale
5.1: benzenesulfonic acid; potassium fluoride / water; dichloromethane / 20 °C / Inert atmosphere; Large scale
View Scheme
tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl)carbamate
1172623-98-1

tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl)carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
1.2: 15 - 25 °C / Inert atmosphere
2.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
4.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
1.2: 15 - 25 °C / Inert atmosphere
2.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
4.1: triethylamine / Inert atmosphere
5.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
1.2: 15 - 25 °C / Inert atmosphere
2.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
4.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / Inert atmosphere
5.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Large scale
1.2: 0 - 20 °C / Large scale
2.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 15 h / 0 - 20 °C / Inert atmosphere; Large scale
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 7.67 h / 0 - 20 °C / Large scale
4.1: benzenesulfonic acid; potassium fluoride / water; dichloromethane / 20 °C / Inert atmosphere; Large scale
View Scheme
tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate
1172623-99-2

tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
2: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
3: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
2: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
3: triethylamine / Inert atmosphere
4: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
2: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
3: sodium hexamethyldisilazane / N,N-dimethyl-formamide / Inert atmosphere
4: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 15 h / 0 - 20 °C / Inert atmosphere; Large scale
2: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 7.67 h / 0 - 20 °C / Large scale
3: benzenesulfonic acid; potassium fluoride / water; dichloromethane / 20 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 3 steps
1: ruthenium trichloride; acetic acid; sodium bromate / water; acetonitrile / 21 h / -5 - 5 °C
2: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -10 °C
3: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 35 °C
View Scheme
6a-hydroxy-3a,4,6,6a-tetrahydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylic acid tert-butyl ester

6a-hydroxy-3a,4,6,6a-tetrahydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylic acid tert-butyl ester

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / dichloromethane; methanol / 0 °C / Inert atmosphere
2.1: sodium hydride / acetonitrile / Inert atmosphere
2.2: Inert atmosphere
3.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
4.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: toluene-4-sulfonic acid / dichloromethane; methanol / 0 °C / Inert atmosphere
2.1: triethylamine / 2-methyltetrahydrofuran / -5 °C / Inert atmosphere
2.2: 1 h / -5 °C / Inert atmosphere
3.1: Isopropyl acetate / 22 °C / Inert atmosphere
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
5.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / dichloromethane; methanol / 0 °C / Inert atmosphere
2: sodium hydride / acetonitrile / Inert atmosphere
3: Isopropyl acetate / 22 °C / Inert atmosphere
4: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
5: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: toluene-4-sulfonic acid / dichloromethane; methanol / 6 h / 0 °C / Large scale
2.1: triethylamine; potassium tert-butylate / 2-methyltetrahydrofuran / 3 h / -10 - 20 °C / Inert atmosphere; Large scale
2.2: 2 h / 20 °C / Inert atmosphere; Large scale
3.1: Isopropyl acetate / 0 - 20 °C / Large scale
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 7.67 h / 0 - 20 °C / Large scale
5.1: benzenesulfonic acid; potassium fluoride / water; dichloromethane / 20 °C / Inert atmosphere; Large scale
View Scheme
tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate
1226781-82-3

tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Isopropyl acetate / 22 °C / Inert atmosphere
2: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
3: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: Isopropyl acetate / 0 - 20 °C / Large scale
2: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / 7.67 h / 0 - 20 °C / Large scale
3: benzenesulfonic acid; potassium fluoride / water; dichloromethane / 20 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 3 steps
1: -15 - 22 °C / Inert atmosphere
2: triethylamine; sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide; water / 1 h / 0 - 2 °C / Inert atmosphere
3: trifluoroacetic acid / N,N-dimethyl acetamide; water / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: isopropyl alcohol; Isopropyl acetate / 25 - 35 °C
2: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -10 °C
3: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 35 °C
View Scheme
Multi-step reaction with 3 steps
1: ethyl acetate / 18 h / 5 - 25 °C / Large scale
2: sodium tris(acetoxy)borohydride; orthoformic acid triethyl ester / N,N-dimethyl acetamide / 12 h / 5 - 50 °C / Inert atmosphere; Large scale
3: benzenesulfonic acid / acetonitrile / 17 h / 5 - 25 °C / Large scale
View Scheme
(±)-tert-butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate
1172623-95-8

(±)-tert-butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
1.2: 2.5 h / -10 - 20 °C / Inert atmosphere
2.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
3.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
4.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
4.2: 15 - 25 °C / Inert atmosphere
5.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
6.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
7.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
1.2: 2.5 h / -10 - 20 °C / Inert atmosphere
2.1: 1,4-diaza-bicyclo[2.2.2]octane; ((R,R)-Ts-DENEB)RuCl; formic acid / tetrahydrofuran / 10 - 35 °C / Inert atmosphere
3.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
4.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
4.2: 15 - 25 °C / Inert atmosphere
5.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
6.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
7.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
1.2: 2.5 h / -10 - 20 °C / Inert atmosphere
2.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
3.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
4.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
4.2: 15 - 25 °C / Inert atmosphere
5.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
6.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
7.1: triethylamine / Inert atmosphere
8.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
D,L-propargylglycine
50428-03-0

D,L-propargylglycine

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium hydroxide / tert-butyl methyl ether; water / 4 h / 20 °C / Inert atmosphere
2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere
2.2: 20 - 25 °C / Inert atmosphere
3.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
3.2: 2.5 h / -10 - 20 °C / Inert atmosphere
4.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
5.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
6.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
6.2: 15 - 25 °C / Inert atmosphere
7.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
8.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
9.1: triethylamine / Inert atmosphere
10.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: sodium hydroxide / tert-butyl methyl ether; water / 4 h / 20 °C / Inert atmosphere
2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere
2.2: 20 - 25 °C / Inert atmosphere
3.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
3.2: 2.5 h / -10 - 20 °C / Inert atmosphere
4.1: 1,4-diaza-bicyclo[2.2.2]octane; ((R,R)-Ts-DENEB)RuCl; formic acid / tetrahydrofuran / 10 - 35 °C / Inert atmosphere
5.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
6.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
6.2: 15 - 25 °C / Inert atmosphere
7.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
8.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
9.1: triethylamine / Inert atmosphere
10.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: sodium hydroxide / tert-butyl methyl ether; water / 4 h / 20 °C / Inert atmosphere
2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere
2.2: 20 - 25 °C / Inert atmosphere
3.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
3.2: 2.5 h / -10 - 20 °C / Inert atmosphere
4.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
5.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
6.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
6.2: 15 - 25 °C / Inert atmosphere
7.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
8.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
9.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / Inert atmosphere
10.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid
61172-66-5

2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere
1.2: 20 - 25 °C / Inert atmosphere
2.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
2.2: 2.5 h / -10 - 20 °C / Inert atmosphere
3.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
4.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
5.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
5.2: 15 - 25 °C / Inert atmosphere
6.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
7.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
8.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere
1.2: 20 - 25 °C / Inert atmosphere
2.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
2.2: 2.5 h / -10 - 20 °C / Inert atmosphere
3.1: 1,4-diaza-bicyclo[2.2.2]octane; ((R,R)-Ts-DENEB)RuCl; formic acid / tetrahydrofuran / 10 - 35 °C / Inert atmosphere
4.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
5.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
5.2: 15 - 25 °C / Inert atmosphere
6.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
7.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
8.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere
1.2: 20 - 25 °C / Inert atmosphere
2.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere
2.2: 2.5 h / -10 - 20 °C / Inert atmosphere
3.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
4.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
5.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
5.2: 15 - 25 °C / Inert atmosphere
6.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
7.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
8.1: triethylamine / Inert atmosphere
9.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
(±)-tert-butyl (1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl)carbamate
1172623-96-9

(±)-tert-butyl (1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl)carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
2.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
3.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
3.2: 15 - 25 °C / Inert atmosphere
4.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
5.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
6.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane; ((R,R)-Ts-DENEB)RuCl; formic acid / tetrahydrofuran / 10 - 35 °C / Inert atmosphere
2.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
3.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
3.2: 15 - 25 °C / Inert atmosphere
4.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
5.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
6.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere
2.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
3.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
3.2: 15 - 25 °C / Inert atmosphere
4.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
5.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
6.1: triethylamine / Inert atmosphere
7.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
tert-butyl ((1R,2S)-1-(2,5-difluorophenyl)-1-hydroxypent-4-yn-2-yl)carbamate

tert-butyl ((1R,2S)-1-(2,5-difluorophenyl)-1-hydroxypent-4-yn-2-yl)carbamate

Omarigliptin
1226781-44-7

Omarigliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
2.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
2.2: 15 - 25 °C / Inert atmosphere
3.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -15 °C / Inert atmosphere
5.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
2.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
2.2: 15 - 25 °C / Inert atmosphere
3.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
5.1: triethylamine / Inert atmosphere
6.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere
2.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere
2.2: 15 - 25 °C / Inert atmosphere
3.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / Inert atmosphere
5.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / Inert atmosphere
6.1: trifluoroacetic acid / water / 5 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: tert-butylammonium hexafluorophosphate(V); sodium salt of N-hydroxysuccinimide / 1,2-dimethoxyethane / 0.17 h / 25 - 35 °C / Inert atmosphere
1.2: 26 h / 40 - 85 °C
2.1: dimethylsulfide borane complex / tert-butyl methyl ether / -10 - -5 °C
2.2: 14 h / 0 - 26 °C
3.1: ruthenium trichloride; acetic acid; sodium bromate / water; acetonitrile / 21 h / -5 - 5 °C
4.1: sodium tris(acetoxy)borohydride / N,N-dimethyl acetamide / -10 °C
5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 35 °C
View Scheme
(methoxymethyl)phosphonoyl dichloride
38075-11-5

(methoxymethyl)phosphonoyl dichloride

Omarigliptin
1226781-44-7

Omarigliptin

alanine isopropyl ester hydrochloride
39613-92-8, 62062-56-0, 62062-65-1

alanine isopropyl ester hydrochloride

isopropyl (2S)-2-[[[[(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-methylsulfonyl-4,6-dihydropyrrolo[3,4-c]pyrazol-5-yl)tetrahydropyran-3-yl]amino](methoxymethyl)phosphoryl]amino]propanoate

isopropyl (2S)-2-[[[[(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-methylsulfonyl-4,6-dihydropyrrolo[3,4-c]pyrazol-5-yl)tetrahydropyran-3-yl]amino](methoxymethyl)phosphoryl]amino]propanoate

Conditions
ConditionsYield
Stage #1: (methoxymethyl)phosphonoyl dichloride; Omarigliptin With triethylamine In tetrahydrofuran at -10 - -5℃; for 1h; Inert atmosphere;
Stage #2: alanine isopropyl ester hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 3h; Inert atmosphere;
32.95%

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