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

HRID 636371Notizen

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Reaktionsgleichung von HRID 636371
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 9824954(5,11-Dihydro-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-[4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-phenyl]-methanoneAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a5df348ba41847a0865b79d8283e352a
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194407B1

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