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

HRID 3596

반응식

HRID 3596 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:31][CH2:32][C:33](Cl)=[O:34]>C(Cl)Cl.CN(C1C=CC=CN=1)C>[Cl:31][CH2:32][C:33]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1)=[O:34]

참가 물질

6

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

생성물 1

HCID 218370752-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]acetamide수율 100.1%

시약·촉매·용매 2

HCID 218852-Dimethylaminopyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 0.91 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]-benzodiazepine in 10 ml of methylene chloride is added 0.46 g of triethylamine and 36 mg of dimethylaminopyridine followed by the slow addition of 0.42 g of chloroacetyl chloride in 5 ml of methylene chloride. The resulting mixture is stirred at room temperature for 3 hours then partitioned with 10 ml of 50% NaHCO3 and the methylene chloride evaporated in vacuo. The remaining suspension is filtered, washed with 50% NaHCO3, H2O, EtOAc (2×2 ml), ether (2×5 ml) and dried in vacuo to give 1.14 g of beige solid. MS(CI): 380(M+H).

후처리

  1. customthen partitioned with 10 ml of 50% NaHCO3
  2. customthe methylene chloride evaporated in vacuo
  3. filtrationThe remaining suspension is filtered
  4. washwashed with 50% NaHCO3, H2O, EtOAc (2×2 ml), ether (2×5 ml)
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-917010d59ebf4aef9603f2501a624c6d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733905

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