2-Chlorobenzoyl chloride → N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-chlorobenzamide

HRID 3492

반응식

HRID 3492 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[CH:33]=[CH:32][C:15]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[CH:29]=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:14][CH:13]=1>C(Cl)Cl>[CH:31]1[CH:30]=[CH:29][N:21]2[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:18]([C:16]([C:15]3[CH:14]=[CH:13][C:12]([NH:11][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[Cl:1])=[CH:33][CH:32]=3)=[O:17])[CH2:19][C:20]=12

참가 물질

4

반응물 2

HCID 691102-Chlorobenzoyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

생성물 1

HCID 10527151N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-chlorobenzamide수율 72.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 347 mg of 2-chlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamineo After stirring for 3 minutes, 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature for 18 hours. The volatiles are concentrated in vacuo to give a residue which is dissolved in methylene chloride, washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried with Na2SO4, filtered and concentrated in vacuo to give a residue which is crystallized from methylene chloride to give 525 mg of the desired product as a white crystalline solid, m.p. 228°-230° C.

후처리

  1. customThe bath is removed
  2. stirringthe reaction mixture stirred at room temperature for 18 hours
  3. concentrationThe volatiles are concentrated in vacuo
  4. customto give a residue which
  5. washwashed with water, 2N citric acid, 1M NaHCO3 and brine
  6. dry with materialThe organic layer is dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a residue which
  10. customis crystallized from methylene chloride

출처 및 근거

ORD 기록
ord-30afe811bcc64b1893cb0de1def7b791
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733905

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