HCID 86712706, compound → HCID 86712707, compound

Participants

Reaction Steps

A slurry of 10% Pd/C (53% water; 0.100 g) in DMF (2 mL) was added to a solution of tert-butyl 4-(4-((5-methoxy-4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A99) (0.112 g, 0.201 mmol) in DMF (8 mL) and TEA (1 mL), and the resulting mixture stirred under an atmosphere of hydrogen at room temperature for 16 hours. The resulting mixture was filtered through a pad of Celite, washing with EtOAc (50 mL). The solvent was removed in vacuo and the resultant residue purified by silica gel column chromatography (Biotage Isolera, 25 g SiO2 cartridge, 0-65% EtOAc in petroleum benzine 40-60° C.) to yield the title compound A100 as a pale yellow oil (0.110 g, 98%); 1H NMR (400 MHz, CDCl3) δ 7.95 (s, 1H), 7.50 (d, J=8.6 Hz, 2H), 7.24-7.14 (m, 4H), 7.11 (d, J=8.5 Hz, 2H), 7.02 (s, 1H), 4.34-4.13 (m, 2H), 3.76 (s, 3H), 3.73 (s, 2H), 3.65 (s, 3H), 3.06-2.98 (m, 2H), 2.98-2.90 (m, 2H), 2.77 (t, J=12.1 Hz, 2H), 2.58 (tt, J=11.9, 3.3 Hz, 1H), 1.78 (d, J=13.0 Hz, 2H), 1.57 (qd, J=12.9, 4.5 Hz, 2H), 1.46 (s, 9H). LCMS-A: rt 6.77 min; m/z 561.4 [M+H]+.

Provenance & Evidence