Acetic Acid → 3-({2-[(4-Carbamimidoyl-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid

HRID 2227633Notes

Reaction equation

HRID 2227633 reaction equation
Cl.[C:2]1([N:8]([CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])[C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][CH:21]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+].C(O)(=O)C>O>[C:2]1([N:8]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH2:28])=[CH:22][CH:21]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 184125531-Methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylicacid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide-hydrochloride

Product 1

HCID 98908823-({2-[(4-Carbamimidoyl-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 300 mg (0.56 mmol) of 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride, 15 ml of ethanol, 4 ml of water and 120 mg (3.0 mmol) of sodium hydroxide was stirred for two hours at room temperature. Then the mixture was diluted with about 20 ml of water and made weakly alkaline with glacial acetic acid. The product which crystallized out was suction filtered, washed with water, and dried at 60° C. in vacuo.

Workup

  1. customThe product which crystallized out
  2. filtrationfiltered
  3. washwashed with water
  4. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-9f3d88a53ec24647aeb35da2910eb55d
Source dataset
uspto-grants-2002_07
Patent number
US06414008B1

Reaction notes

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