Dimethylformamide → (5,11-Dihydro-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-[4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-phenyl]-methanone

HRID 636371

반응식

HRID 636371 반응식
[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]([F:35])([F:34])[C:24]1[CH:32]=[C:31](F)[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27].C[N:37]([CH3:40])C=O>O>[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[N:10]([C:26]([C:25]3[CH:29]=[CH:30][C:31]([N:37]4[CH:40]=[CH:9][C:8]([CH3:15])=[N:7]4)=[CH:32][C:24]=3[C:23]([F:35])([F:34])[F:22])=[O:27])[CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 11430Potassium CarbonateHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

생성물 1

HCID 9824954(5,11-Dihydro-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-[4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-phenyl]-methanone수율 33.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine of Example 1, Step B (10.6 g, 53.8 mmol) in dimethylformamide (125 mL) under nitrogen was added potassium carbonate (22.4 g, 162 mmol). The mixture was cooled and treated dropwise with a solution of crude 2-trifluoromethyl-4-fluorobenzoyl chloride of Step A (81 mmol) in dimethylformamide (25 mL). After stirring at room temperature for 2 hours, the mixture was diluted with water and extracted with dichloromethane. The organic extracts were dried over magnesium sulfate and evaporated to dryness. The crude material was dissolved in dichloromethane and purified by flash chromatography (on silica Merck-60, hexane-ethyl acetate 80:20) to provide the pure title compound (6.9 g, 33.1%) which was crystallized by sonication from ethanol-hexane, m.p. 183-185° C.

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. customevaporated to dryness
  5. dissolutionThe crude material was dissolved in dichloromethane
  6. custompurified by flash chromatography (on silica Merck-60, hexane-ethyl acetate 80:20)

출처 및 근거

ORD 기록
ord-a5df348ba41847a0865b79d8283e352a
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194407B1

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