Chloroform methanol → HCID 178424524, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of 4-cyano-1H-imidazole-2-carboxylic acid [4-acetyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (6.00 g, 0.0160 mol) in 100 mL of THF at −78° C. was added a solution of MeMgBr (3.0 M in THF, 22 mL, 0.066 mol) via syringe over a 20-min period. The reaction was allowed to warm to ca. 0° C. over a 30-min period at which point there was no starting material evident by thin layer chromatography (10% MeOH—CHCl3). The reaction was cooled to −78° C., quenched by the addition of saturated aqueous NH4Cl (100 mL) and allowed to warm to 0° C. The mixture was extracted with ether (2×150 mL) and dried (Na2SO4). The solvent was concentrated to afford the title compound as a white solid (6.40 g, 100%). The NMR and mass spectral data were identical to those for the compound produced in Example 14, step (d).

Provenance & Evidence