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CAS No.: | 1226781-44-7 |
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Name: | Omarigliptin (MK-3102) |
Article Data: | 15 |
Molecular Structure: | |
Formula: | C17H20F2N4O3S |
Molecular Weight: | 398.434 |
Synonyms: | mk-3102; |
EINECS: | 682-558-0 |
Density: | 1.61±0.1 g/cm3(Predicted) |
Boiling Point: | 529.4±60.0 °C(Predicted) |
PSA: | 98.83000 |
LogP: | 2.86110 |
Omarigliptin
Conditions | Yield |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |