Pyrazole → HCID 54767498, compound

HRID 598751Notes

Reaction equation

HRID 598751 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2([C:33]([F:36])([F:35])[F:34])[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28](F)=[C:27]([CH3:32])[CH:26]=3)[CH2:21]2)[CH:16]=[C:17]([Cl:19])[CH:18]=1>CN(C)C=O>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2([C:33]([F:35])([F:34])[F:36])[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([N:7]4[CH:11]=[CH:10][CH:9]=[N:8]4)=[C:27]([CH3:32])[CH:26]=3)[CH2:21]2)[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 58223544HCID 58223544, compound

Product 1

HCID 54767498HCID 54767498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of potassium carbonate (1.0 g, 7.24 mmol) and pyrazole (0.50 g, 7.35 mmol) in N,N-dimethylformamide (5 mL) was added 5-(3,5-dichlorophenyl)-3-(4-fluoro-3-methylphenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole (i.e. the product from Step B) (0.50 g, 1.27 mmol). The reaction mixture was stirred vigorously for 36 h at 120° C. Then the reaction mixture was absorbed onto silica gel, concentrated, and purified by flash chromatography on silica gel and eluted with a gradient of 0-25% ethyl acetate in hexane to afford the title product, a compound of the present invention, as a yellow oil (32.0 mg).

Workup

  1. customThen the reaction mixture was absorbed onto silica gel
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel
  4. washeluted with a gradient of 0-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3e6c45e2557247b5a96841874eb9a190
Source dataset
uspto-grants-2011_03
Patent number
US07897630B2

Reaction notes

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