Acetic Acid → 3-[[1-methyl-2-[[4-(N-octoxycarbonylcarbamimidoyl)anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid

HRID 50309Notes

Reaction equation

HRID 50309 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:42][CH2:43][C:44]([O:46]C)=[O:45])[C:8]([C:10]1[CH:41]=[CH:40][C:13]2[N:14]([CH3:39])[C:15]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[NH:38])[NH:26][C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:28])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9].[OH-].[Na+].CO.C(O)(=O)C>O.C(OCC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:42][CH2:43][C:44]([OH:46])=[O:45])[C:8]([C:10]1[CH:41]=[CH:40][C:13]2[N:14]([CH3:39])[C:15]([CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:25](=[NH:38])[NH:26][C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:28])=[CH:23][CH:24]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 140409603methyl 3-[[1-methyl-2-[[4-(N-octoxycarbonylcarbamimidoyl)anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate

Product 1

HCID 1404435013-[[1-methyl-2-[[4-(N-octoxycarbonylcarbamimidoyl)anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acidYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

0.7 g (1.1 mmol) of 1-methyl-2-[N-[4-(N-n-octyloxycarbonylamidino)phenyl]aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)amide was stirred in a mixture of 0.12 g (3.0 mmol) of sodium hydroxide, 5 mL of water, and 10 mL of methanol for one hour at room temperature. Then the mixture was diluted with 20 mL of water and adjusted to pH 6 with glacial acetic acid. Then about 5 mL of diethylether were added and the mixture was vigorously stirred for one hour. The product thus precipitated was suction filtered, washed with a little water, then with diethylether and dried. Yield: 80% of theory, C34H41N7O5 (627.8); EKA mass spectrum: (M+H)+=628; (M+H+Na)++=325.7; (M+Na)+=650; (M+2Na)++=337.7.

Workup

  1. customThe product thus precipitated
  2. filtrationfiltered
  3. washwashed with a little water
  4. dry with materialwith diethylether and dried

Sources & evidence

ORD record
ord-f9657518cd8e4a65823335069e47d94b
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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