HCID 68784936, compound → 4-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[1-(2-isopropylpyrimidin-4-yl)piperidin-4-yl]methyl}benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[1-(2-isopropenylpyrimidin-4-yl)piperidin-4-yl]methyl}benzamide (10 mg) in 1.33 ml of methanol and 0.66 ml of tetrahydrofuran was added 3 mg of 10% palladium on carbon. This mixture was evacuated and flushed with a hydrogen-filled balloon ten times. The reaction mixture was stirred at 50° C. for 1 h, and then at room temperature for 15 h. The mixture was then filtered through a plug of Celite, eluting with methanol. After concentration of the eluent in vacuo, the residue was further purified by filtration through a plug of silica gel, eluting with ethyl acetate. Concentration of the residue in vacuo provided the title compound (112 mg, 93%). Mass spectrum (ESI) 523.4 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.3 Hz, 2H), 8.16 (d, J=6.2 Hz, 1H), 7.95 (d, J=8.0 Hz, 3H), 7.52 (s, 1H), 6.32 (m, 3H), 4.52 (d, J=9.1 Hz, 2H), 3.46 (m, 3H), 2.97 (sept, J=6.9 Hz, 1H), 2.91 (t, J=11.3 Hz, 2H), 2.00 (s, 1H), 1.88 (d, J=12.1 Hz, 2H), 1.46 (d, J=6.8, 6H), 1.33 (m, 2H), 1.28 (d, J=6.9, 6H).

Provenance & Evidence