Imidazole → HCID 23523859, compound

HRID 2420665Notes

Reaction equation

HRID 2420665 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:19])[NH:12][NH:13][C:14]=2[C:15]([F:18])([F:17])[F:16])=[CH:5][CH:4]=1)[CH3:2].[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].N1C=CN=C1.O>CN(C)C=O.C(OCC)(=O)C>[Si:20]([O:19][C:11]1[C:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)=[C:14]([C:15]([F:17])([F:18])[F:16])[NH:13][N:12]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 106357234-(4-Ethylbenzyl)-5-(trifluoromethyl)-1H-pyrazole-3-ol

Product 1

HCID 23523859HCID 23523859, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2-Dihydro-4-((4-ethylphenyl)methyl)-5-(trifluoromethyl)-3H-pyrazol-3-one (4) (prepared by the method described in J. Med. Chem 1996, 39, 3920-3928) (15.0 g; 55.6 mmol) was dissolved in dimethylformamide (150 ml) and cooled to 0° C. t-Butyldimethylsilyl chloride (9.3 g; 61.1 mmol) was added in portions, and then, imidazole (4.2 g; 61.1 mmol) was added in portions. Then, the resulting mixture was back to ambient temperature, then the mixture was stirred for 3 hours. Water was added to the reaction solution, for extraction twice with ethyl acetate. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, to give the desired compound (21.4 g; 55.6 mmol). (100%)

Workup

  1. additionwas added in portions
  2. customwas back to ambient temperature
  3. washThe organic phase was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3fb514b46f2a499082bbf5a5df16ef7e
Source dataset
uspto-grants-2011_06
Patent number
US07956041B2

Reaction notes

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