D-Psicose → HCID 86712713, compound

Participants

Reaction Steps

A suspension of 10% Pd/C (0.050 g) and tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-4-(trifluoromethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A106) (0.196 g, 0.295 mmol) in DMF (20 mL) was stirred under a hydrogen atmosphere at 50 Psi pressure for 24 hours. The resulting mixture was filtered through Celite, washing with MeOH (2×50 mL). The filtrate was adsorbed onto silica gel then purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.) to give the title compound A107 as a light yellow liquid (0.157 g, 80%); 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 7.54 (d, J=8.5 Hz, 2H), 7.52-7.43 (m, 3H), 7.35 (d, J=7.8 Hz, 1H), 7.20 (d, J=8.5 Hz, 2H), 4.25 (brs, 2H), 3.79 (s, 2H), 3.70 (s, 3H), 3.17 (m, 2H), 3.09 (m, 2H), 2.81 (t, J=11.4 Hz, 2H), 2.70-2.56 (m, 1H), 1.83 (d, J=12.7 Hz, 2H), 1.72-1.55 (m, 2H), 1.49 (s, 9H). LCMS-A: rt 7.199 min; m/z 667.3 [M+H]+.

Provenance & Evidence