1,1'-Carbonyldiimidazole → HCID 58416754, compound

Participants

Reaction Steps

A solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (5) (0.98 g, 4.26 mmol) in DCM (4.0 mL) was added dropwise over 1 hr, to a suspension of CDI (0.69 g, 4.26 mmol) in DCM (3.0 mL) and the mixture was stirred at RT for 2 hr. This solution was then added dropwise to a solution of the naphthylamine (71) (0.90 g, 2.37 mmol) in DCM (10 mL), such that after each 1.0 mL aliquot was added, the reaction was stirred for 1 hr. The reaction was quenched with MeOH (20 mL), and silica was added (20 g) and the volatiles were evaporated in vacuo. The residue was subjected to purification by column chromatography (100 g, 50 to 100% EtOAc in isohexane, gradient elution). The resulting product was triturated from DCM (20 mL) and the solid collected, and washed with diethyl ether (50 mL) to give the title compound (Intermediate P) as a purple solid (0.48 g, 38%): m/z 523 (M+H)+ (ES+).

Provenance & Evidence