Ethylamine → N-[3-(7-Ethylamino-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamide

Participants

Reaction Conditions

Reaction Steps

N-[3-(7-Chloro-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamide (50 mg, 0.106 mmol) is mixed with ethylamine (0.14 mL 70% in water, 2.2 mmol) in a sealed tube. 1 mL of n-butanol is added and the reaction is stirred at 100° C. for 16 hours. After cooling and removal of solvent under vacuum, the crude product is dissolved in DMSO and purified by reverse phase preparative HPLC to give the final product as white solid: 1H NMR 400 MHz (DMSO-d6) δ 10.47 (s, 1H), 8.48 (s, 1H), 8.29 (s, 1H), 8.25 (d, 1H, J=8.0 Hz), 7.96 (d, 1H, J=7.8 Hz), 7.78 (m, 2H), 7.66 (m, 2H), 7.26 (d, 1H, J=9.0 Hz), 6.46 (s, 1H), 3.57 (s, 3H), 3.39 (q, 2H, J=7.1 Hz), 2.13 (s, 3H), 1.22 (t, 3H, J=7.1 Hz); MS m/z 481.2 (M+1).

Provenance & Evidence