Nicotinoyl chloride → methyl 3-[[1-methyl-2-[[4-[N-(pyridine-3-carbonyl)carbamimidoyl]anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate

HRID 50317Notes

Reaction equation

HRID 50317 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][CH3:37])=[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].[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[N:41][CH:40]=1>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][CH3:37])=[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:38](=[O:45])[C:39]4[CH:44]=[CH:43][CH:42]=[N:41][CH:40]=4)=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 184125161-Methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)amide Hydrochloride

Product 1

HCID 140409616methyl 3-[[1-methyl-2-[[4-[N-(pyridine-3-carbonyl)carbamimidoyl]anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoateYield 40%

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-methoxycarbonylethyl)amide hydrochloride and nicotinic acid chloride. Yield: 40% of theory, C32H30N8O4 (590.7); Rf value: 0.47 (silica gel; dichloromethane/methanol=9:1); EKA mass spectrum: (M+H)+=591; (M+H+Na)++=307; (M+Na)+=613.

Sources & evidence

ORD record
ord-c0d3f073985f4b9faebac40e87933729
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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