Trifluoroacetic acid → Ethyl 2-(3-((5-cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclohexyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 3-((5-cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclohexyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (67 mg, 0.13 mmol) in dichloromethane (1 mL) was treated with TFA (500 μL) and stirred for 1 hr at rt. The reaction was concentrated in vacuo and then diluted with NMP (1 mL) and then treated with Hunig's base (110 μL, 0.67 mmol) followed by ethyl 2-chlorobenzo[d]thiazole-6-carboxylate (33 mg, 0.13 mmol). After heating overnight at 120° C., the reaction was poured into water and extracted with EtOAc. The organic phase was collected, dried (MgSO4), filtered, and concentrated. The crude residue was purified by chromatography (SiO2, linear gradient, 0-60%, EtOAc in Hexanes) to give the title compound.

Provenance & Evidence