HCID 25171033, compound → HCID 68745687, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2yl)benzoyl]amino}methyl)piperidine-1-carboxylate (2.19 g, EXAMPLE 35) in methanol (30 ml) and tetrahydrofuran (7 ml) was added 10% palladium on carbon (500 mg, 4.70 mmol). The mixture was flushed with nitrogen, then flushed with hydrogen, and then warmed to 50° C. and stirred for 3 h under a hydrogen balloon at this temperature, at which point LC/MS analysis showed no starting material. The mixture was filtered through a plug of Celite, washing liberally with methanol, and then concentrated to provide the title compound (1.7 g, 103%). Mass spectrum (ESI) 403.6 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.32 (d, J=8 Hz, 2H), 7.94 (d, J=8.5 Hz, 2H), 7.93 (s, 1H), 7.51 (s, 1H), 6.33 (br s, 1H), 3.44-3.54 (m, 2H), 3.40 (m, 2H), 3.13 (br d, 2H), 2.63 (br t, 2H), 1.77 (m, 2H), 1.46 (d, J=6.5 Hz, 6H), 1.26 (m, 2H).

Provenance & Evidence