Imidazole → HCID 23523859, compound

HRID 1071910Notes

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>[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

Conditions

Temperature: 0 °C

Procedure

15.0 g (55.6 mmol) of 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) was dissolved in 150 ml of dimethylformamide, and cooled to 0° C. Then, 9.3 g (61.1 mmol) of t-butyl dimethylsilyl chloride was added to the above solution in small portions, and thereafter 4.2 g (61.1 mmol) of imidazole was added in small portions. The temperature of the resultant mixture was returned to room temperature and the mixture was stirred for 3 hours. After the addition of water to the reaction mixture, the reaction mixture was extracted with ethyl acetate twice. The resultant organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and concentrated, to give 21.4 g (55.6 mmol) of the intended compound (100% yield).

Workup

customwas returned to room temperature
extractionthe reaction mixture was extracted with ethyl acetate twice
washThe resultant organic layer was washed with a saturated sodium chloride aqueous solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-465d2a1678e44de6a9a899559a51feee
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908905B2

Reaction notes

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