Carbonochloridic acid, 2-(methylsulfonyl)ethyl ester → ethyl 3-[[1-methyl-2-[[4-[N-(2-methylsulfonylethoxycarbonyl)carbamimidoyl]anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate

HRID 50310Notes

Reaction equation

HRID 50310 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:9]([C:11]1[CH:31]=[CH:30][C:14]2[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)=[O:10].Cl[C:40]([O:42][CH2:43][CH2:44][S:45]([CH3:48])(=[O:47])=[O:46])=[O:41]>ClCCl.CO>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:9]([C:11]1[CH:31]=[CH:30][C:14]2[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH:28][C:40]([O:42][CH2:43][CH2:44][S:45]([CH3:48])(=[O:47])=[O:46])=[O:41])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 104458Carbonochloridic acid, 2-(methylsulfonyl)ethyl esterHCID 18412337Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo(d)imidazole-5-carboxamido)propanoate hydrochloride

Product 1

HCID 140409602ethyl 3-[[1-methyl-2-[[4-[N-(2-methylsulfonylethoxycarbonyl)carbamimidoyl]anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoateYield 65%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 90 from 1-methyl-2-[N-(4-amidinophenyl) aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride and 2-(methylsulfonyl)ethyl chloroformate. Yield: 65% of theory, C31H35N7O7S (649.7); Rf value: 0.54 (silica gel; dichloromethane/methanol=9:1); EKA mass spectrum: (M+H)+=650; (M+H+Na)++=336.6; (M+Na)+=672; (M+2Na)++=347.6.

Sources & evidence

ORD record
ord-a542682735564f659640337a27eed1c8
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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