Acetone → HCID 57518318, compound

HRID 1408541Notes

Reaction equation

HRID 1408541 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:26](SC)=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([CH:18]3[CH2:20][CH2:19]3)=[CH:16][C:15]([C:21]([F:24])([F:23])[F:22])=[N:14]2)=[CH:9][CH:8]=1)=[O:5].O[O:32][S:33]([O-:35])=O.[K+].[CH3:37]C(C)=O>O>[Cl:1][C:2]1[CH:28]=[CH:27][C:26]([S:33]([CH3:37])(=[O:35])=[O:32])=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17]([CH:18]3[CH2:20][CH2:19]3)=[CH:16][C:15]([C:21]([F:23])([F:22])[F:24])=[N:14]2)=[CH:11][CH:12]=1)=[O:5]

Participants

5

Reactant 3

HCID 180AcetoneHCID 23707502Potassium hydroxy sulfiteHCID 51353105HCID 51353105, compound

Product 1

HCID 57518318HCID 57518318, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-chloro-N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}-5-(methylthio)benzamide (40 mg, 0.08 mmols) was dissolved in a 5 mL mixture of H2O and acetone (1:1) at 0° C. and added Oxone (108 mg, 0.16 mmols). The mixture was stirred at ambient temperature for one hour. The reaction mixture was filtered to remove oxone and filtrate was worked up (AcOEt: H2O). Title compound (38 mg) was obtained as a white solid. M.P. 132-135° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.97 (s, 1H), 8.19 (d, J 2.2, 1H), 8.04 (dd, J 8.4, 2.2, 1H), 7.89 (d, J 8.6, 3H), 7.65 (d, J 8.8, 2H), 6.62 (s, 1H), 3.30 (s, 3H), 1.97-1.81 (m, 1H), 0.99-0.94 (m, 2H), 0.86-0.79 (m, 2H). MS (m/z): 481.85 [M−H]−.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove oxone and filtrate

Sources & evidence

ORD record
ord-2fef9de5c76e4b2493ac2e2a43bbff7a
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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