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

HRID 50320Notes

Reaction equation

HRID 50320 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[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:39]([O:41][CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45])=[O:40]>ClCCl.C(O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[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:39]([O:41][CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45])=[O:40])=[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 18412300HCID 18412300, compound

Product 1

HCID 140409597ethyl 2-[[1-methyl-2-[[4-[N-(2-methylsulfonylethoxycarbonyl)carbamimidoyl]anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]acetateYield 72%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 90 from 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-ethoxycarbonylmethylamide hydrochloride and 2-(methylsulfonyl)ethyl chloroformate. Yield: 72% of theory, C30H33N7O7S (635.7); Rf value: 0.23 (silica gel; dichloromethane/ethanol=19:1); EKA mass spectrum: (M+H)+=636; (M+H+Na)++=329.8.

Sources & evidence

ORD record
ord-274c7b37a4f04b3b97210d67b1b31259
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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