565452-98-4

Basic information

• Product Name: 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)- (9CI)
• Synonyms: 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)- (9CI);(2R)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile;(R)-1-(2-Chloroacetyl)pyrrolidine-2-carbonitrile;Vildagliptin Impurity 7;(R)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile
• CAS NO: 565452-98-4
• Molecular Formula: C7H9ClN2O
• Molecular Weight: 172.61216
• Product Categories: ACETYLHALIDE;Heterocycles, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 565452-98-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 363.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -4.65±0.40(Predicted)
• CAS DataBase Reference: 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)- (9CI)(565452-98-4)
• EPA Substance Registry System: 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)- (9CI)(565452-98-4)

Safety Data

• Hazardous Substances Data: 565452-98-4(Hazardous Substances Data)

Usage

Uses

(2R)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile, can be used in the synthesis of 1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine, and Vildagliptin (C363780), which are potent, selective, and orally bioavailable dipeptidyl peptidase IV Inhibitor with Antihyperglycemic properties, that might be used for the treatment of type 2 diabetes.

Upstream product

• 214398-99-9 (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide 
• 7531-52-4 L-prolinamide 
• 147-85-3 L-proline 
• 62937-45-5 (R)-prolinamide 

Downstream Products

• 739366-20-2 (S)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid {2-[(2-cyanopyrrolidin-1-yl)-2-oxoethylamino]-2-methylpropyl}amide 
• 739365-95-8 tert-butyl N-[2-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)-2-methylpropyl]carbamate 

Relevant articles and documents

Preparation method of isomer impurities of vildagliptin

The invention discloses a preparation method of isomer impurities of vildagliptin, and relates to the technical fields of medicine and chemical industry. The preparation method comprises the steps: S1: enabling D-prolinamide (I) serving as a raw material to react with chloroacetyl chloride to obtain a reaction product (II), and then enabling the reaction product (II) to react with trifluoroacetic anhydride to obtain a reaction product (III); S2: enabling the reaction product (III) to react with 3-amino-1-adamantanol to generate a target product (IV). The preparation method disclosed by the invention has the advantages that the preparation process is simple, the operation is simple and convenient, reaction time is short, and the post-treatment purification is simple and effective, which is beneficial to industrialized production. The purity of manufactured impurities of the vildagliptin is high and is as high as 99.1% through HPLC (high-performance liquid chromatography) detection. By further studying the isomer impurities of the vildagliptin, the quality of the vildagliptin can be better controlled, and the drug safety is improved.

COMPOUND INHIBITING DIPEPTIDYL PEPTIDASE IV

The invention aims to provide a dipeptidyl peptidase IV inhibitor which is satisfactory in respect of activity, stability and safety and has an excellent action as a pharmaceutical agent. The invention is directed to a compound represented by the following general formula or a pharmaceutically acceptable salt thereof: wherein R1 and R2 each represents hydrogen, an optionally substituted C1-6 alkyl group, or -COOR5 whereupon R5 represents hydrogen or an optionally substituted C1-6 alkyl group, or R1 and R2, together with a carbon atom to which they are bound, represent a 3- to 6-membered cycloalkyl group, R3 represents hydrogen or an optionally substituted C6-10 aryl group, R4 represents a hydrogen or a cyano group, D represents -CONR6-, -CO- or -NR6CO-, R6 represents hydrogen or an optionally substituted C1-6 alkyl group, E represents -(CH2)m- whereupon m is an integer of 1 to 3, -CH2OCH2-, or -SCH2-, n is an integer of 0 to 3, and A represents an optionally substituted bicyclic heterocyclic group or bicyclic hydrocarbon group.