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Impurity of ethyl 3-(2-(((4-carbamimidoylphenyl) amino) methyl)-1-methyl-N-(pyridin-2- yl)-1H benzo[d]imidazole-5-carboxamido) propanoate hydrochloride

IP.com Disclosure Number: IPCOM000235562D
Publication Date: 2014-Mar-10
Document File: 2 page(s) / 34K

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The IP.com Prior Art Database

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Impurity of ethyl 3-(2-(((4-carbamimidoylphenyl) amino) methyl)-1-methyl-N-(pyridin-2- yl)-1H benzo[d]imidazole-5-carboxamido) propanoate hydrochloride

    Ethyl 3-(2-(((4-carbamimidoylphenyl) amino) methyl)-1-methyl-N-(pyridin-2-yl)- 1Hbenzo[d]imidazole-5-carboxamido) propanoate hydrochloride (referred to as compound A) has the following structure.

Compound A

An impurity of Compound A and process for preparation thereof is disclosed herein after.

Impurity I: Isopropyl 3-(2-(((4-carbamimidoylphenyl) amino) methyl)-1-methyl-N- (pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate hydrochloride

Impurity I has the following structure:

Impurity I

Example 1: Preparation of Impurity I:

    To a suspension of 3-(2-(((4-Carbamimidoyl phenyl) amino)methyl)-1-methyl-N- (pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido) propanoic acid ( 15 gm) in isopropanol (750 ml), isopropyl alcohol hydrochloride was added (470 ml) and the reaction mass heated to a temperature of about 78°C followed by cooling of the mixture to room temprature. The mixture was concentrated and ethanol (500 ml) was charged to the residue followed by pH adjustment (approximately to about 8) by using ethanolic ammonia. The reaction mass was stirred for 15 minutes and concentrated completely under vacuum. The product was isolated by usual work up

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using water and acetone. The obtained solid was filtered and dried under vacuum at 60-65° to give impurity 1.

H1NMR (400 MHz): 1.14(t, 6H), 2.66(t,...