Triethylamine → N-[4-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)phenyl]-2-methylbenzamide

HRID 3537

반응식

HRID 3537 반응식
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)=[O:5].C(N(CC)CC)C.[N:27]1[N:36]2[C:30]([CH2:31][NH:32][C:33]3[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=3[CH2:35]2)=[CH:29][CH:28]=1>C(Cl)Cl.C(OCC)(=O)C>[N:27]1[N:36]2[C:30]([CH2:31][N:32]([C:11]([C:10]3[CH:14]=[CH:15][C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=4[CH3:1])=[CH:8][CH:9]=3)=[O:12])[C:33]3[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=3[CH2:35]2)=[CH:29][CH:28]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl ChlorideHCID 130628255,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine

생성물 1

HCID 21837012N-[4-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)phenyl]-2-methylbenzamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 1.37 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 15 ml of methylene chloride, cooled to 0° C. is added 1.5 ml of triethylamine. To the mixture is added 5 mmol of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine. The reaction mixture is allowed to stir at room temperature for 48 hours and the volatiles are removed in vacuo to give a residue. The residue is dissolved in 100 ml of ethyl acetate and washed with water, 2N citric acid, aqueous NaHCO3 and brine. The solution is dried with Na2SO4 and the solvent removed in vacuo. The residue is purified by flash chromatography on silica gel with ethyl acetate-hexane to give the desired product, m.p. 142°-146° C.

후처리

  1. customthe volatiles are removed in vacuo
  2. customto give a residue
  3. washwashed with water, 2N citric acid, aqueous NaHCO3 and brine
  4. dry with materialThe solution is dried with Na2SO4
  5. customthe solvent removed in vacuo
  6. customThe residue is purified by flash chromatography on silica gel with ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-640af18f5f2a4182aa628a6af14296b2
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733905

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