Acetic Acid → 6-Benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-carboxybenzimidazole

HRID 276051Notes

Reaction equation

HRID 276051 reaction equation
C(N(CC)CC)C.[C:8]1([S:14]([NH:17][C:18](=[O:40])[C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:30][CH:29]=3)[CH:20]=2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[K+].[C:43]([OH:46])(=[O:45])[CH3:44]>CN(C)C=O.CO>[C:8]1([S:14]([NH:17][C:18]([C:19]2[CH:24]=[CH:23][C:22]3[N:25]=[C:44]([C:43]([OH:46])=[O:45])[N:26]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)=[CH:30][CH:29]=4)[C:21]=3[CH:20]=2)=[O:40])(=[O:15])=[O:16])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 53635937N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide

Product 1

HCID 543733606-Benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-carboxybenzimidazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.080 g) and 0.148 g of methyloxalyl chloride were added to a solution of 0.400 g of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide in 3 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, and the residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 9:1) to obtain crude 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-carboxybenzimidazole. This compound was dissolved in 1 ml of acetic acid and 5 ml of methanol, and the mixture was stirred at 60° C. for 15 hours. The reaction solution was neutralized with a potassium hydroxide aqueous solution. The crystals precipitated were separated through filtration, and were dried to give 0.245 g of 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-carboxybenzimidazole (229).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified through silica-gel column chromatography (eluent
  3. additiona mixture of ethyl acetate and methanol at a ratio of 9:1)
  4. customto obtain crude 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-carboxybenzimidazole
  5. customThe crystals precipitated
  6. customwere separated through filtration
  7. customwere dried

Sources & evidence

ORD record
ord-ad56c51d02c940499d296ccea13b7ffd
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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