Vildagliptin NEW

Chinese name: Vidaletine

English name: Vildagliptin

CAS: 274901-16-5

Molecular formula: C16H15F6N5O? H3O4P? H2O

MDL number: MFCD08275142

Molecular weight: 303.4

category

API: lipid-regulating drug

Melting point: 153-155? C

Specific rotation: -78.3° (c = 9.73 in methanol)

Boiling point: 531.3±50.0 °C(Predicted)

Density: 1.27

Flash point: 275.1 ° C

Storage conditions: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

Solubility: Soluble in DMSO (up to 45mg/ml), DMF (up to 20mg/ml) or ethanol (up to 20mg/ml).

Acidity coefficient (pKa) : 15.05±0.40(Predicted)

Form: solid

Color: White

Stability: Can be stored in DMSO, DMF or ethanol solution at -20°C for up to 3 months

InChI: InChI = 1 s/C17H25N3O2 / c18-9-14-2-9-14-2 (14) and 15 (21) 10-19-16-10-19-16-13 (6-16) 8-17 (22, 7-12) 11-16 / h12-14,19,22 H, 1-8 -, 10-11 h2 / t12? And 13? , 14 and 16? , 17? /m0/s1

InChIKey: SYOKIDBDQMKNDQ-XWTIBIIYSA-N

SMILES: N1(C(CNC23CC4CC(CC(O)(C4)C2)C3)=O)CCC[C@H]1C#N

effect

Vigliptin is a selective, competitive and reversible inhibitor of DPP24

Synthesis method L-proline is protected by di-tert-butyl dicarbonate, and then carbonyl amination with ammonia gas occurs under the action of 1-(3-dimethylaminopropyl) -3-ethylcarbodiimide (EDC), and then L-proline (intermediate 4) is obtained by removing Boc protection group with hydrochloric acid. L-proline Chemicalbook amide is acylated to (S) -chloro-acetyl-2-aminoacylpyrrolidine (intermediate 2), dehydrated to (S) -n-chloro-acetyl-2-cyanopyrrolidine (intermediate 3), and then nucleophilic substitution reaction with 3-amino-1-amantadanol (4) is performed to obtain Vigagliptin.