HCID 86712658, compound → HCID 86712659, compound

Participants

Reaction Steps

A solution of tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-2-methylphenyl)piperidine-1-carboxylate (A41) (0.248 g, 0.407 mmol) in EtOH (10 mL) was added to a solution of 10% Pd/C (53% water; 0.680 g) in DMF (6 mL). The resulting mixture was stirred at room temperature for 16 hours under an atmosphere of hydrogen then filtered through a pad of Celite, washing with EtOAc (80 mL). The volatiles were removed in vacuo to afford a yellow oil which was purified by silica gel column chromatography (Biotage Isolera, 25 g SiO2 cartridge, 0-40% EtOAc in petroleum benzine 40-60° C.) to yield the title compound A42 as a clear oil (0.196 g, 79%); 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 7.61 (s, 1H), 7.51 (dd, J=7.9, 1.5 Hz, 1H), 7.39 (d, J=2.2 Hz, 1H), 7.29-7.19 (m, obscured by solvent), 7.17 (d, J=8.4 Hz, 1H), 4.42-4.18 (m, 2H), 3.75 (s, 2H), 3.67 (s, 3H), 3.19-3.03 (m, 4H), 2.90-2.73 (m, 3H), 2.37 (s, 3H), 1.75 (d, J=12.6 Hz, 2H), 1.62 (m, 2H), 1.50 (s, 9H). LCMS-A: rt 7.094 min; m/z 613.2 [M+H]+.

Provenance & Evidence