Ethanol → 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-1-phenyl-1H-pyrazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

4-[(4-cyano-1-phenyl-1H-pyrazol-3-yl)amino]-N,N-dimethylbenzamide (83 mg, 0.250 mmol) and 5 N sodium hydroxide (0.351 mL, 1.753 mmol) were taken up in DMSO (1 mL)/EtOH (1 mL) and warmed to 60° C. Hydrogen peroxide (0.329 mL, 3.76 mmol) was added dropwise and stirring continued at 60° C. for 15 minutes. Room temperature was attained, water was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine (×2), dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC (25-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc followed by 15% MeOH—CHCl3) gave 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-1-phenyl-1H-pyrazole-4-carboxamide as a pale yellow solid.

Provenance & Evidence