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Basic Information
| CAS No.: | 274901-16-5 |
|---|---|
| Name: | Vildagliptin |
| Article Data: | 40 |
| Molecular Structure: | |
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|
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| Formula: | C17H25N3O2 |
| Molecular Weight: | 303.404 |
| Synonyms: | 2-Pyrrolidinecarbonitrile,1-[[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-, (2S)- (9CI);Galvus;LAF 237;NVP-LAF 237;(-)-(2s)-1-(((3-hydroxytricyclo(3.3.1.1(3,7))dec-1-yl)amino)acetyl)pyrrolidine-2-carbonitrile; |
| EINECS: | 630-410-0 |
| Density: | 1.27 g/cm3 |
| Melting Point: | 153-155?C |
| Boiling Point: | 531.3 °C at 760 mmHg |
| Flash Point: | 275.1 °C |
| Appearance: | white crystalline powder |
| Risk Codes: | 28-38-41-48 |
| Safety: | 24/25-26-28-36/37/39 |
| PSA: | 76.36000 |
| LogP: | 1.50308 |
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Synthetic route
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| With sodium carbonate; sodium chloride In dichloromethane at 20 - 40℃; Product distribution / selectivity; | 95% |
| With sodium carbonate In water at 40℃; for 0.0333333h; Product distribution / selectivity; | 75% |
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| With palladium on activated charcoal; ammonium formate In tetrahydrofuran at 20℃; for 8h; Reagent/catalyst; Solvent; Temperature; | 91.9% |
| With palladium on activated charcoal; ammonium formate In tetrahydrofuran at 20℃; for 10h; Solvent; Reagent/catalyst; Temperature; | 91.9% |
- 1032564-18-3
(3-hydroxyadamantan-1-ylamino)acetic acid
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: C12H14N2O3S With sodium hydroxide In dichloromethane at 0℃; for 1.5h; Stage #2: (3-hydroxyadamantan-1-ylamino)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; Concentration; | 90.8% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: C16H33NOSi2; (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile at 75 - 80℃; for 3h; Stage #2: With ethanol In acetonitrile for 2h; Reagent/catalyst; | 88.3% |
- 702-82-9
3-aminoadamantan-1-ol
- 207557-35-5
(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate; potassium iodide In tetrahydrofuran; butanone at 40℃; for 3h; | 82% |
| With potassium carbonate; potassium iodide In tetrahydrofuran; butanone at 40℃; for 3h; Reflux; | 82% |
| With potassium carbonate; potassium iodide In acetone at 50 - 55℃; for 3h; Solvent; | 82.2% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: (S)-pyrrolidine-2-carbonitrile p-toluenesulfonate; chloroacetyl chloride With triethylamine In dichloromethane at 0 - 5℃; for 2h; Stage #2: 3-aminoadamantan-1-ol In water for 4h; Temperature; Reflux; | 76.9% |
...Expand
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: (S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carboxylic acid amide With trifluoroacetic acid; trifluoroacetic anhydride In 2-methyltetrahydrofuran Reflux; Stage #2: With potassium carbonate In 2-methyltetrahydrofuran; water at 5 - 10℃; Reagent/catalyst; | 75% |
| With trichlorophosphate In dichloromethane at 10℃; for 4h; Reagent/catalyst; Solvent; Temperature; Time; Reflux; | 4.53 g |
- 702-82-9
3-aminoadamantan-1-ol
- 214398-99-9
(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide With trifluoroacetic anhydride In tetrahydrofuran at 20℃; for 2h; Cooling with ice; Stage #2: 3-aminoadamantan-1-ol With potassium carbonate; potassium iodide In tetrahydrofuran at 40℃; for 8.5h; Time; Reflux; | 71% |
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| With palladium 10% on activated carbon; hydrogen In methanol at 20℃; | 61.5% |
| With palladium 10% on activated carbon; hydrogen In methanol for 22h; |
- 214398-99-9
(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide
- 274901-16-5
vildagliptin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 7.82 g / trifluoroacetic anhydride / tetrahydrofuran / 1 h / 20 °C 2: K2CO3 / tetrahydrofuran / 0 - 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 2: potassium carbonate; potassium iodide / tetrahydrofuran / 5 h / 60 - 65 °C View Scheme | |
| Multi-step reaction with 2 steps 1.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 4 h / 35 - 48 °C 2.1: potassium carbonate; potassium iodide / butanone / 40 °C 2.2: 3 h / 38 - 75 °C View Scheme | |
| Multi-step reaction with 2 steps 1.1: trichlorophosphate / -5 - 20 °C 2.1: potassium carbonate; potassium iodide / acetone / 0.25 h / 20 °C 2.2: 40 - 65 °C View Scheme |
Raw Materials
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