1350800-77-9

Basic information

• Product Name: 1H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-3,6-dione, hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)-
• Synonyms: 1H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-3,6-dione, hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)-;Saxagliptin Dione Impurity;Saxagliptin Impurity 7;(1aS,4S,6aR,7aS)-4-(3-hydroxy-1-adamantyl)-1a,4,5,6a,7,7a-hexahydro-1H-cyclopropa[3,4]pyrrolo[3,5-c]pyrazine-3,6-dione
• CAS NO: 1350800-77-9
• Molecular Formula: C18H24N2O3
• Molecular Weight: 316.39476
• EINECS: -0
• Mol File: 1350800-77-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-3,6-dione, hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-3,6-dione, hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)-(1350800-77-9)
• EPA Substance Registry System: 1H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-3,6-dione, hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)-(1350800-77-9)

Safety Data

• Hazardous Substances Data: 1350800-77-9(Hazardous Substances Data)

Usage

Uses

Saxagliptin Cyclic Amide is a degradation product of Saxagliptin (S143500); a potent and selective reversible inhibitor of dipeptidyl peptidase-4 (DPP-IV) developed for the treatment of type 2 diabetes.

Relevant articles and documents

Kinetic and mechanistic insight into the thermodynamic degradation of saxagliptin

The dipeptidyl peptidase-IV inhibitor saxagliptin (Onglyza) can undergo a thermodynamically favored cyclization to form the corresponding cyclic amidine. The kinetics and mechanism of this conversion were examined to develop a commercial synthesis that afforded saxagliptin with only trace levels of this key byproduct. Important findings of this work are the identification of a profound solvent effect and the determination of an autocatalytic pathway. Both of these phenomena result from transition structures involving proton transfer (Figure presented).