Trichloroacetyl chloride → 2,2,2-Trichloro-1-{10-[(2-methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

HRID 639237노트

반응식

HRID 639237 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]3[CH:22]=[CH:23][CH:24]=[C:13]3[CH2:12]2)=[O:10])[CH:6]=[CH:5][C:4]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].C(N(CC)CC)C.[Cl:39][C:40]([Cl:45])([Cl:44])[C:41](Cl)=[O:42].C(OCC)(=O)C>ClCCl.C(Cl)(Cl)Cl>[Cl:39][C:40]([Cl:45])([Cl:44])[C:41]([C:22]1[N:14]2[C:13]([CH2:12][N:11]([C:9]([C:7]3[CH:6]=[CH:5][C:4]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])=[C:3]([O:2][CH3:1])[CH:8]=3)=[O:10])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15]2)=[CH:24][CH:23]=1)=[O:42]

참가 물질

7

반응물 4

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 6867947010-[(2-Methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

생성물 1

HCID 160388252,2,2-Trichloro-1-{10-[(2-methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone수율 87.7%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

A solution of 10-[(2-methoxy-2′-methyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step E (21 mmol) and triethylamine (43 mmol) in anhydrous dichloromethane (45 mL) was cooled in an ice bath. To the stirred solution was added, dropwise, trichloroacetyl chloride (65 mmol). The mixture was allowed to stir at ambient temperature for 72 hours, then was washed with 0.1 N hydrochloric acid and brine, and dried over anhydrous sodium sulfate. Evaporation yielded a foam that solidified by heating with ethyl acetate and chloroform to provide 10.2 g (85%) of the title compound as a white solid, m.p. 221-222° C. MS [(+)ESI, m/z]: 553 [M+H]+

후처리

  1. additionTo the stirred solution was added
  2. washwas washed with 0.1 N hydrochloric acid and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation
  5. customyielded a foam that solidified

출처 및 근거

ORD 기록
ord-f0d1bddc9dba46c7981cc08e749090af
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691848B2

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