tert-Butyl 4-(4-((4-((2-(2-amino-2-oxoethyl)-4-fluorophenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate → HCID 86712656, compound

Participants

Reaction Steps

A suspension of 10% Pd/C (0.175 g) and tert-butyl 4-(4-((4-((2-(2-amino-2-oxoethyl)-4-fluorophenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A36) (0.191 g, 0.320 mmol) in DMF (10 mL) and Et3N (1 mL) was stirred under an atmosphere of hydrogen for 16 hours. The resulting mixture was diluted with EtOAc (60 mL), filtered through Celite and the volatiles were removed under reduced pressure. The residue was adsorbed onto silica gel, then purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A37 as a yellow solid (0.168 g, 87%); 1H NMR (400 MHz, d6-DMSO) δ 10.14 (s, 1H), 8.65 (s, 1H), 7.65 (d, J=8.6 Hz, 2H), 7.48 (s, 1H), 7.23-7.15 (m, 3H), 7.08 (dd, J=10.2, 2.8 Hz, 1H), 7.00 (td, J=8.4, 2.7 Hz, 2H), 4.07 (d, J=11.8 Hz, 2H), 3.50 (s, 2H), 3.13-3.04 (m, 2H), 3.04-2.95 (m, 2H), 2.79 (brs, 2H), 2.69-2.57 (m, 1H), 1.74 (d, J=12.9 Hz, 2H), 1.54-1.43 (m, 2H), 1.42 (s, 9H). LCMS-A: rt 6.612 min; m/z 602 [M+H]+.

Provenance & Evidence