Hydrochloric Acid → 1-Methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(methoxycarbonylmethyl)amide Dihydrochloride

HRID 50268Notes

Reaction equation

HRID 50268 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:8]([C:10]1[CH:29]=[CH:28][C:13]2[N:14]([CH3:27])[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:35].CO.C(=O)([O-])[O-].[NH4+:42].[NH4+]>ClCCl.C(O)C>[ClH:35].[ClH:35].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:8]([C:10]1[CH:29]=[CH:28][C:13]2[N:14]([CH3:27])[C:15]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[NH:42])[NH2:26])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 517111Ammonium CarbonateHCID 184122921-Methyl-2-[n-(4-cyanophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(methoxycarbonylmethyl)-amide

Product 1

HCID 184126601-Methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(methoxycarbonylmethyl)amide DihydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 25d from 1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(methoxycarbonylmethyl)amide and methanolic hydrochloric acid, methanol, and ammonium carbonate. Yield: 73% of theory, C2H25N7O3 (471.5); Rf value: 0.12 (silica gel; dichloromethane/ethanol=4:1); EKA mass spectrum: (M+H)+=472; (M+H+Na)++=247.8.

Sources & evidence

ORD record
ord-37e4e4793b6f41b3b0656b8f25064ad8
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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