Hydrochloric Acid → Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo(d)imidazole-5-carboxamido)propanoate hydrochloride

HRID 50289Notes

Reaction equation

HRID 50289 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:8]([C:10]1[CH:30]=[CH:29][C:13]2[N:14]([CH2:27]C)[C:15]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9].[ClH:38].C(O)C.C(=O)([O-])[O-].[NH4+:46].[NH4+]>ClCCl.CO>[ClH:38].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:8]([C:10]1[CH:30]=[CH:29][C:13]2[N:14]([CH3:27])[C:15]([CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:25](=[NH:26])[NH2:46])=[CH:23][CH:24]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 517111Ammonium CarbonateHCID 184124691-ethyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 18412337Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo(d)imidazole-5-carboxamido)propanoate hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 25d from 1-ethyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide and ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 85% of theory, C28H31N7O3 (513.6); Rf value: 0.21 (silica gel; dichloromethane/methanol=5:1); EKA mass spectrum: (M+H)+=514; (M+H+Na)++=268.6; (M+2H)++=257.7.

Sources & evidence

ORD record
ord-6df13b9bf1204101b07973a170a25fe6
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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