144625-34-3

Upstream product

• 945540-18-1 4-[(α-N-pentanoylamino)cyclopentamidomethyl]-2'-carboxamidobiphenyl 
• 133690-92-3 [(2'-cyanobiphenyl-4-yl)methyl]amine 
• 866946-42-1 2-(4-aminomethylphenyl)benzamide 
• 15026-80-9 N-pentanoylaminocyclopentane-1-carboxylic acid 

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 
• 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 academic research and scientific papers

Process for preparation of Irbesartan

A process for the preparation of Irbesartan of formula (I) using the steps of: (i) reacting 4′ aminomethyl-2-cyano biphenyl of formula (VI) with 1-veleramido cyclopentane carboxylic acid of formula (V) ?in an organic solvent and in the presence of an acid, without activating the —COOH group of compound of formula (V) to give 1-(2′cyanobiphenyl-4-yl-methylaminocarbonyl)-1-pentanoylamino cyclopentane of formula (VII). ?converting the compound of formula (VII) obtained in step (i) to Irbesartan of formula (I) by reacting the compound of the formula (VII) with tributyl tin azide in o-xylene to give Irbesartan of formula (I).

AN IMPROVED PROCESS FOR PREPARATION OF IRBESARTAN

A process for the preparation of Irbesartan of formula (I): Formula (I) comprising the steps of: (i) reacting 4' aminomethyl-2-cyano biphenyl of formula (VI) with 1-veleramido cyclopentane carboxylic acid of formula (V): Formula (VI) and Formula (V) in an organic solvent and in the presence of an acid, without activating the -COOH group of compound of formula (V) to give 1-(2'cyanobiphenyl-4-yl-methylaminocarbonyl)-1-pentanoylamino cyclopentane of formula (VII). Formula (VII) converting the compound of formula (VII) obtained in step (i) to Irbesartan of formula (I) by reacting the compound of the formula (VII) with tributyl tin azide in o-xylene to give Irbesartan of formula (I).

AN IMPROVED PROCESS FOR THE PREPARATION OF IRBESARTAN

The present invention relates to an improved process for the preparation of 2-n-butyl-3-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]-1,3-diazaspiro[4.4]non-1-en-4-one (Irbesartan)

A novel approach for the conversion of primary amides into tetrazoles by using tributyltin chloride and sodium azide in the presence of DMF

A novel and efficient one-pot synthesis of tetrazole derivatives such as Irbesartan and its analogues has been described from the primary acid amide derivatives. Thus 2-alkyl-3-[p-(o-ami-dophenyl (benzyl]-1.3-diazaspiro[4.4]non- 1-en-4-one derivatives or 4-[α-(acylamino)cyclopentamidomethyl]-2′- carboxamidobiphenyl derivatives were treated with tributyltin chloride and sodium azide in o-xylene in the presence of DMF to afford irbesartan and its analogues without generation of nitriles. The synthesis of these new starting materials is also described, and two of the derivatives have been used as new intermediates in the preparation of irbesartan. Georg Thieme Verlag Stuttgart.