141745-71-3

Basic information

• Product Name: 1-[(2'-Cyano[1,1'-biphenyl]-4-yl)MethylaMino]-N-pentanoylcyclopentanecarboxaMide
• Synonyms: 1-[(2'-Cyano[1,1'-biphenyl]-4-yl)MethylaMino]-N-pentanoylcyclopentanecarboxaMide;N-[(2'-Cyano[1,1'-biphenyl]-4-yl)Methyl]-1-[(1-oxopentyl)aMino]cyclopentanecarboxaMide
• CAS NO: 141745-71-3
• Molecular Formula: C₂₅H₂₉N₃O₂
• Molecular Weight: 403.51666
• Product Categories: Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 141745-71-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-[(2'-Cyano[1,1'-biphenyl]-4-yl)MethylaMino]-N-pentanoylcyclopentanecarboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2'-Cyano[1,1'-biphenyl]-4-yl)MethylaMino]-N-pentanoylcyclopentanecarboxaMide(141745-71-3)
• EPA Substance Registry System: 1-[(2'-Cyano[1,1'-biphenyl]-4-yl)MethylaMino]-N-pentanoylcyclopentanecarboxaMide(141745-71-3)

Safety Data

• Hazardous Substances Data: 141745-71-3(Hazardous Substances Data)

Usage

Uses

An impurity of Irbesartan (I751000).

Upstream product

• 52-52-8 1-amino-1-cyclopentanecarboxylic acid 
• 177219-40-8 1-(pentanoylamino)cyclopentanecarboxamide 
• 114772-54-2 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile 
• 16195-83-8 1-aminocyclopentanecarbonitrile hydrochloride 
• 638-29-9 n-valeryl chloride 
• 194984-24-2 1-cyano-1-n-pentanoylaminocyclopentane 
• 15026-80-9 N-pentanoylaminocyclopentane-1-carboxylic acid 
• 133690-92-3 [(2'-cyanobiphenyl-4-yl)methyl]amine 

Downstream Products

• 138402-11-6 2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one 
• 329055-23-4 2-n-butyl-4-spirocyclopentane-1-[((2'-tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one hydrochloride 
• 138401-24-8 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile 

Relevant articles and documents

A new process for the preparation of irbesartan

A process for the preparation of Irbesartan or a pharmaceutically acceptable salt thereof comprising the step of coupling the 1-pentanamidocyclapentanecarboxamide of formula (V) with 4'-substituted methyl biphenyl-2-carbonitrile or 1-(4'-substituted methyl biphenyl-2-yl)-1H-tetrazole wherein tetrazole can be protected or unprotected to obtain the N-[(2'-cyanobiphenyl-4-yl)methyl]-1-pentanamidocyclopentanecarboxamide or N-[1-({[2'-(1H-tetrazol-1-yl)biphenyl-4-yl]methylamino)methyl)cydopentyl]pentanamide wherein tetrazole can be protected or unprotected that is further processed to Irbesartan or a pharmaceutical acceptable salt thereof.

Improved methods for the synthesis of irbesartan, an antihypertensive active pharmaceutical ingredient

New methods for the preparation of irbesartan 1 have been described. The dehydration and tetrazole formation in one step from substituted cyclopentane derivative 7 with tributyltin chloride and sodium azide is described. Selective hydrolysis of nitrile 3 with HCl has also been described in the preparation of N-acylaminocyclopentane-2-carboxylic acid 4, which is the key intermediate for the preparation of irbesartan. The impurity profiling of irbesartan has also been discussed. Copyright Taylor & Francis Group, LLC.

PROCESS FOR PREPARING IRBESARTAN

A process for preparing irbesartan comprises pentanoylation of cycloleucine in the presence of sodium hydroxide to form n-pentanoyl cycloleucine, condensing this product with 2-(4-aminomethyl phenyl) benzonitrile using dicyclohexyl carbodiimide and 1-hydroxy benzotriazole as a catalyst to form the 4-(?-N-pentanoyl amino) cyclopentamido methyl-2'-cyano biphenyl compound, and then cyclizing using trifluroacetic acid in the presence of an aromatic solvent to form cyano irbesartan. Cyano irbesartan is converted to irbesartan by reaction with tributyltin chloride and sodium azide in the presence of an aromatic solvent.