HCID 58902337, compound → HCID 58902314, compound

Participants

Reaction Steps

A slurry of 7-{[2-(acetylamino)pyridin-4-yl]oxy}-N-[4-cyano-3-(trifluoromethyl)-phenyl]-2-naphthamide (I-157) (163 mg, 0.33 mmol) and Raney Nickel (2800 slurry in water, 50% v/v, approx 8 mg) in THF (5 mL) and 7.0 M ammonia in MeOH (5 mL), was allowed to stir under an atmosphere of hydrogen for 18 h. After this time, additional Raney Nickel was added and hydrogenation continued for a further 18 h. The reaction mixture was filtered through Celite and washed with THF and MeOH. The filtrate was concentrated and purified by column chromatography. The product was dissolved in MeOH and 2M HCl in Et2O was added. The solvents were evaporated to give 7-{[2-(acetylamino)pyridin-4-yl]oxy}-N-[4-(aminomethyl)-3-(trifluoromethyl)phenyl]-2-naphthamide (I-151) as an off-white solid (45 mg, 23%). 1H NMR (400 MHz, d6-DMSO): δ 11.27 (s, 1H), 10.97 (s, 1H), 8.67 (s, 1H), 8.63 (br.s, 2H), 8.36 (d, 1H), 8.28 (d, 1H), 8.24-8.16 (m, 3H), 8.09-8.06 (m, 1H), 7.93 (d, 1H), 7.55 (dd, 1H), 7.45 (d, 1H), 6.96 (dd, 1H), 4.15-4.11 (m, 2H), and 2.08 (s, 3H). LCMS: (FA) ES+ 495.4.

Provenance & Evidence