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

HRID 1276912노트

반응식

HRID 1276912 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6fd8eb0a7fa84845b470106dd673c54d
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166219

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