Sodium Hydroxide → 1-Methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(3-hydroxycarbonylpropyl)amide Hydrochloride

HRID 50246Notes

Reaction equation

[ClH:1].Cl.[C:3]1([N:9]([CH2:33][CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])[C:10]([C:12]2[CH:32]=[CH:31][C:15]3[N:16]([CH3:30])[C:17]([CH2:19][NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27](=[NH:29])[NH2:28])=[CH:23][CH:22]=4)=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>>[ClH:1].[C:3]1([N:9]([CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])[C:10]([C:12]2[CH:32]=[CH:31][C:15]3[N:16]([CH3:30])[C:17]([CH2:19][NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27](=[NH:28])[NH2:29])=[CH:23][CH:22]=4)=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 184126771-Methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylicacid-N-phenyl-N-(3-ethoxycarbonylpropyl)-amide-dihydrochloride

Product 1

HCID 184123851-Methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(3-hydroxycarbonylpropyl)amide HydrochlorideYield 73.5%

Procedure

Prepared analogously to Example 26 from 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(3-ethoxycarbonylpropyl)amide dihydrochloride and sodium hydroxide solution. Yield: 73.5% of theory, C27H28N6O3 (484.6); EKA mass spectrum: (M+H)+=485; (M+2H)++=243; (M+H+Na)++=254.

Sources & evidence

ORD record: ord-0ab96f2a93904c43baacdb8086dbc109
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710055B2

Reaction notes

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