Water → HCID 58724570, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil; 15 mg, 0.375 mmol) is added to a cooled (˜0° C.) solution of 1-methyl-5-phenyl-1H-pyrazole-4-carboxylic acid ((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amide (of Example 91; 100 mg, 0.3 mmol) in dry dimethylformamide (10 mL) and the mixture is allowed to stir for 30 min. Methyl iodide (30 μL, 0.49 mmol) is added and the solution is stirred at room temperature until the reaction is complete, as judged by TLC. Water is added and the solution is extracted twice with ethyl acetate. The combined organic layers are washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified by C-18 reversed phase HPLC with a gradient of 10-100% acetonitrile/water containing 0.1% TFA as a modifier to give 1-methyl-5-phenyl-1H-pyrazole-4-carboxylic acid methyl-((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amide.

Provenance & Evidence