HCID 86712729, compound → HCID 86712730, compound

Participants

Reaction Steps

A suspension of 10% Pd/C (53% water; 0.020 g) and tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate (A125) (0.092 g, 0.17 mmol) in DMF (5 mL) and Et3N (0.5 mL) was stirred at room temperature for 18 hours under a hydrogen atmosphere. The resulting mixture was filtered through Celite, and the filter cake washed with EtOAc (250 mL). The combined filtrates were washed with water (3×100 mL) and brine (3×100 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-100% EtOAc in hexanes) to give the title compound A126 as a pale brown oil (80 mg, 86%); 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.89 (s, 1H), 7.51 (d, J=0.4 Hz, 1H), 7.25-7.15 (m, 4H), 6.92 (s, 1H), 4.31-4.15 (m, 3H), 3.70 (s, 2H), 3.66 (s, 3H), 3.08 (dd, J=9.4, 6.3 Hz, 2H), 2.90 (dd, J=9.5, 6.3 Hz, 4H), 2.15-2.07 (m, 2H), 2.05 (s, 3H), 2.00-1.85 (m, 2H), 1.46 (s, 9H). LCMS-A: rt 6.195 min; m/z 535.3 [M+H]+.

Provenance & Evidence