Ethyl chloroformate → ethyl 3-[[2-[[4-(N-ethoxycarbonylcarbamimidoyl)-2-methoxyanilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate

HRID 50408Notes

Reaction equation

HRID 50408 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:9]([C:11]1[CH:33]=[CH:32][C:14]2[N:15]([CH3:31])[C:16]([CH2:18][NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][C:21]=3[O:29][CH3:30])=[N:17][C:13]=2[CH:12]=1)=[O:10].Cl[C:42]([O:44][CH2:45][CH3:46])=[O:43]>ClCCl.C(O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:9]([C:11]1[CH:33]=[CH:32][C:14]2[N:15]([CH3:31])[C:16]([CH2:18][NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH:28][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:22][C:21]=3[O:29][CH3:30])=[N:17][C:13]=2[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 184125881-methyl-2-[N-(4-amidino-2-methoxyphenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride

Product 1

HCID 140435597ethyl 3-[[2-[[4-(N-ethoxycarbonylcarbamimidoyl)-2-methoxyanilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoateYield 43%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 90 from 1-methyl-2-[N-(4-amidino-2-methoxyphenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride and ethyl chloroformate. Yield: 43% of theory, C31H35N7O6 (601.7); Rf value: 0.44 (silica gel; dichloromethane/ethanol=9:1); EKA mass spectrum: (M+H)+=602; (M+H+Na)++=312.8.

Sources & evidence

ORD record
ord-5dc62979ca4c42168aa4d7d26543768d
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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