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

HRID 2244227노트

반응식

HRID 2244227 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][N:19]3[CH:27]=[CH:28][CH:29]=[C:18]3[CH2:17]2)=[O:15])[CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:36][C:37]([Cl:42])([Cl:41])[C:38](Cl)=[O:39]>O1CCCC1.C(OCC)(=O)C>[Cl:36][C:37]([Cl:42])([Cl:41])[C:38]([C:27]1[N:19]2[C:18]([CH2:17][N:16]([C:14]([C:10]3[CH:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[CH:13]=[CH:12][CH:11]=3)=[O:15])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20]2)=[CH:29][CH:28]=1)=[O:39]

참가 물질

6

반응물 3

HCID 6420Trichloroacetyl chlorideHCID 10340Sodium CarbonateHCID 6868820210-[(2'-Methyl-1,1'-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

생성물 1

HCID 686873312,2,2-Trichloro-1-{10-[(2'-methyl-1,1'-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone수율 50.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 10-[(2′-methyl-1,1′-biphenyl-3-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step B (1.7 g, 4.5 mmol) and sodium carbonate (0.95 g, 9.0 mmol) in dry tetrahydrofuran (40 mL) was added dropwise trichloroacetyl chloride (0.75 mL, 6.7 mmol) and the reaction mixture stirred at room temperature under nitrogen for 18 hours. The reaction mixture was then diluted with ethyl acetate (150 mL), washed with 1 M hydrochloric acid (150 mL), water (150 mL) and brine (150 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a dark foam. Purification by flash chromatography using a solvent gradient of 60% to 80% dichloromethane in hexane afforded a white solid that was recrystallized from hot ethyl acetate to give the title compound (1.2 g, 50%) as a white needles.

후처리

  1. washwashed with 1 M hydrochloric acid (150 mL), water (150 mL) and brine (150 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a dark foam
  5. customPurification by flash chromatography
  6. customafforded a white solid
  7. customthat was recrystallized from hot ethyl acetate

출처 및 근거

ORD 기록
ord-f7fbb80d9afa46d4b40674c92c3e56f8
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678787B2

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