Hydrochloric Acid → 1-Methyl-2-[2-(2-amidinothiophen-5-yl)ethyl]-benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide-hydrochloride

HRID 50259Notes

Reaction equation

HRID 50259 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:8]([C:10]1[CH:28]=[CH:27][C:13]2[N:14]([CH3:26])[C:15]([CH2:17][CH2:18][C:19]3[S:23][C:22]([C:24]#[N:25])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9].[ClH:36].C(O)C.C(=O)([O-])[O-].[NH4+:44].[NH4+]>ClCCl.CO>[ClH:36].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:8]([C:10]1[CH:28]=[CH:27][C:13]2[N:14]([CH3:26])[C:15]([CH2:17][CH2:18][C:19]3[S:23][C:22]([C:24](=[NH:44])[NH2:25])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 517111Ammonium CarbonateHCID 184124051-Methyl-2-[2-(2-cyanothiophen-5-yl)ethyl]benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide

Product 1

HCID 184124711-Methyl-2-[2-(2-amidinothiophen-5-yl)ethyl]-benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide-hydrochlorideYield 53%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 25d from 1-methyl-2-[2-(2-cyanothiophen-5-yl)ethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide and ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 53% of theory, C26H28N6O3S (504.6); Rf value: 0.22 (silica gel; dichloromethane/methanol=5:1); EKA mass spectrum: (M+H)+=505; (M+H+Na)++=264.

Sources & evidence

ORD record
ord-5f251c25243c4bb4b02d4495901cb401
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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