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

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

Used in Pharmaceutical Synthesis:
2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)(9CI) is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in the Synthesis of Dipeptidyl Peptidase IV Inhibitors:
In the pharmaceutical industry, 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)(9CI) is used as a starting material for the synthesis of 1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine and Vildagliptin (C363780). These compounds are potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitors with antihyperglycemic properties. They have the potential to be used for the treatment of type 2 diabetes, offering a new approach to managing blood sugar levels and improving the quality of life for patients with this condition.

Upstream product

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

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.

A method for synthesizing allah Geleg sandbank (by machine translation)

The invention relates to a method for preparing anti-II type diabetes drug allah Geleg sandbank method for the synthesis of bulk drug (Anagliptin). The lack of commercial synthetic allah Geleg sandbank solve the technical problems of the method. Synthetic method comprises the following steps : (1) with vinyl ether and trichloro acetyl chloride as the raw material, passes through the three-step reaction to obtain the aldehyde protected intermediates 4 ; The 3-amino-5-methyl pyrazole condensation for dehydrating and gets pyrazolo pyrimidine mother nucleus; Carboxy b ester hydrolysis to obtain 2-methyl-pyrazolo [1,5-a] pyrimidin 6-carboxylic acid 6 ; (2) to L-proline as a raw material, passes through the methyl esterification, ammoniation, acetylation, Carbonitride reaction to obtain the chiral cyano pyrrolizinone intermediate 11 ; Chiral cyano pyrrolizinone intermediate 11 And diamine fragment 12 In alkaline conditions to obtain intermediate affinity substituted 13 ; Finally, intermediate 13 Under the conditions of the hydrochloric acid removal protection Boc base namely obtain cyanopentanoyl Azolylamine intermediate 14 ; (3) 2-methyl-pyrazolo [1,5-a] pyrimidine-6-carboxylic acid 6 The cyano Azolylamine intermediate 14 The condensation conditions to obtain the bulk drug allah Geleg sandbank coupled. (by machine translation)

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.

1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: A potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties

Dipeptidyl peptidase IV (DPP-IV) inhibition has the potential to become a valuable therapy for type 2 diabetes. The synthesis and structure - activity relationship of a new DPP-IV inhibitor class, N-substituted-glycyl-2-cyanopyrrolidines, are described as well as the path that led from clinical development compound 1-[2-[5-cyanopyridin-2-yl)amino]ethylamino]acetyl-2-cyano-(S)pyrrolidine (NVP-DPP728, 8c) to its follow-up, 1-[[(3-hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)pyrrolidine (NVP-LAF237, 12j). The pharmacological profile of 12j in obese Zucker fa/fa rats along with pharmacokinetic profile comparison of 8c and 12j in normal cynomolgus monkeys is discussed. The results suggest that 12j is a potent, stable, selective DPP-IV inhibitor possessing excellent oral bioavailability and potent antihyperglycemic activity with potential for once-a-day administration.