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
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inquiryOmarigliptin 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
Cas:1226781-44-7
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inquiry1. 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
Cas:1226781-44-7
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inquiryCangzhou 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
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inquiryDayangChem 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
Cas:1226781-44-7
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inquiryhebei 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
Cas:1226781-44-7
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inquiryOur 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 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;
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
Cas:1226781-44-7
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inquiryWITH 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
Cas:1226781-44-7
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inquiryAdvantages: 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
Cas:1226781-44-7
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inquiry1.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
Cas:1226781-44-7
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inquiryOur 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
Cas:1226781-44-7
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inquiryOmarigliptin (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
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inquiryHello, 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
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inquiryWe 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
Cas:1226781-44-7
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inquiryHenan 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
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inquiryAppearance: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
Cas:1226781-44-7
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Type:Lab/Research institutions
inquiryOmarigliptin (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
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inquiryOur 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-
Cas:1226781-44-7
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inquiryOur 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
Cas:1226781-44-7
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inquiryCompany 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
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
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
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inquiryMassive 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
Cas:1226781-44-7
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inquiryZibo 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
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
Cas:1226781-44-7
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inquiryProduct 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
Cas:1226781-44-7
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryProduct 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,
Cas:1226781-44-7
Min.Order:1 Gram
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inquiryOur 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
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inquiryOmarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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% |
Omarigliptin
Conditions | Yield |
---|---|
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
tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate
Omarigliptin
Conditions | Yield |
---|---|
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
2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
Conditions | Yield |
---|---|
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 |
Omarigliptin
Conditions | Yield |
---|---|
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
Omarigliptin
alanine isopropyl ester hydrochloride
Conditions | Yield |
---|---|
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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