N-(4-(2-(1-Isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)-phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide → N-(4-(2-(1-Isopropylpiperidin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-(4-(2-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide (100 mg, 0.18 mmol, Example 28), HCO2N44 (227 mg, 3.6 mmol, Aldrich) in butanol (2 mL) was added palladium hydroxide (8.3 mg, 0.016 mmol, 20 wt. % Pd (dry basis) on carbon, Aldrich), and the mixture was heated to 120° C. for 16 h with stirring under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered through Celite® pad. The filter cake was washed with MeOH and the combined filtrates were evaporated under reduced pressure. The residue was purified by silica gel column chromatography (7% MeOH/DCM) to provide the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 556 (M+1).

Provenance & Evidence