Reaction Steps
6-(6,7-Dimethoxyquinazolin-4-yloxy)-1-naphthoic acid (37.6 mg, 0.1 mmol) and 4 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (38.4 mg, 0.2 mmol), hydroxybenzotriazole (16.2 mg, 0.12 mmol), triethylamine (40.4 mg, 0.4 mmol) and o-phenylenediamine (43.2 mg, 0.4 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 200 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (39.1 mg, 84%) as a brown solid. 1H NMR (DMSO-d6) δ 4.01 (s, 6H, 2×OCH3), 4.97 (s, 2H, benzene-NH2), 6.65 (t, J=7.2 Hz, 1H, Ar—H), 6.82 (d, J=7.0 Hz, 1H, Ar—H), 7.00 (t, J=7.1 Hz, 1H, Ar—H), 7.38 (d, J=7.1 Hz, 1H, Ar—H), 7.42 (s, 1H, Ar—H), 7.60 (dd, J=2.4 and 9.2 Hz, 1H, Ar—H), 7.64-7.68 (m, 2H, Ar—H), 7.87 (d, J=6.7 Hz, 1H, Ar—H), 7.97 (d, J=2.3 Hz, 1H, Ar—H), 8.09 (d, J=8.2 Hz, 1H, Ar—H), 8.38 (d, J=9.2 Hz, 1H, Ar—H), 8.54 (s, 1H, Ar—H), 9.85 (s, 1H, benzene-NH). LC-MS (m/z) 467 (M+1).
