Tetrahydrofuran → 1-(4-(2-(2-Aminopyridin-4-yloxy)ethyl)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea

Participants

Reaction Steps

To a suspension of CDI (122 mg, 0.752 mmol) in DCM (2 mL) was added a solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (172 mg, 0.752 mmol) in DCM (2.0 mL) and the reaction mixture was stirred at RT for 16 hr. An aliquot (1.0 mL) of this reaction mixture was added to a stirred suspension of 4-(2-(4-aminonaphthalen-1-yl)ethoxy)pyridin-2-amine (34) (42 mg, 0.150 mmol) in DCM (2.0 mL). THF (0.5 mL) was added and the reaction mixture was stirred for 1 hr. A second aliquot (1.0 mL) of the CDI reaction mixture was added and the mixture was stirred for a further 20 hr at RT. Methanol was added and stirring continued for 30 min. The solvent was evaporated and the residue was purified by flash column chromatography (SiO2, 0-5% MeOH in DCM, gradient elution). The resulting impure product was dissolved in ethyl acetate, washed with water and brine, dried (MgSO4) and evaporated in vacuo to afford the title compound (Intermediate F) (42 mg, 52%); m/z 535 (M+H)+, (ES+).

Provenance & Evidence