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

HRID 50273

Reaction equation

HRID 50273 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[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].Cl>C(O)CCCCC>[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH2:38][CH2:3][CH2:4][CH2:5][CH3:6])=[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])[NH2:28])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18412337Ethyl 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo(d)imidazole-5-carboxamido)propanoate hydrochloride

Product 1

HCID 184125031-Methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-n-hexyloxycarbonylethyl)amide HydrochlorideYield 53%

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Procedure

0.60 g (1.1 mmol) of 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride were added to about 30 mL of n-hexanol saturated with hydrogen chloride and the mixture was stirred for 19 hours at room temperature. Then the hexanol was distilled off in vacuo, the residue was mixed with about 5 mL of 1N ammonia solution with stirring, and evaporated down once more. The crude product thus obtained was purified by column chromatography (silica gel, dichloromethane/methanol=5:1). Yield: 53% of theory, C31H37N7O3 (555.7); Rf value: 0.36 (silica gel; dichloromethane/methanol=5:1); EKA mass spectrum: (M+H)+=556.

Workup

  1. distillationThen the hexanol was distilled off in vacuo
  2. additionthe residue was mixed with about 5 mL of 1N ammonia solution
  3. stirringwith stirring
  4. customevaporated down once more

Sources & evidence

ORD record
ord-4d1832ce30f0448394e3e90a4bfaca2e
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Linked notes

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