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ノート

反応式

HRID 636371 の反応式
[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

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 11430Potassium CarbonateHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a5df348ba41847a0865b79d8283e352a
出典データセット
uspto-grants-2001_02
特許番号
US06194407B1

反応ノート

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