1,1'-Carbonyldiimidazole → tert-Butyl 4-(1-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

Participants

Reaction Steps

A solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (5) 612 mg, 2.67 mmol) in DCM (2.0 mL) was added dropwise over 1.5 hr to a suspension of CDI (433 mg, 2.67 mmol) in DCM (2.0 mL) under nitrogen and the solution was stirred at RT for 1 hr. A solution of the naphthyl amine (55) (700 mg, 1.78 mmol) in DCM (4.0 mL) was added in a single portion and the solution was stirred for 16 hr, during which time a precipitate formed. The reaction mixture was taken up in DCM (10 mL) and purified by flash column chromatography (SiO2, 80 g, 0-20% EtOAc in isohexane, gradient elution) to afford the title compound (56) (0.59 g, 50%): m/z 649 (M+H)+ (ES+)

Provenance & Evidence