Reaction Steps
1-{3-[(1-Isopropylpiperidin-4-yl)oxy]phenyl}methanamine (188 mg, 0.757 mmol) and methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (244 mg, 0.757 mmol) were dissolved in MeOH (2 ml). The reaction was heated in a microwave at 120° C. for 15 minutes, during which time a precipitate had been formed in the microwave vial. The precipitate was filtered off and washed with MeOH. The filtrate was purified by reversed phase HPLC yielding the title compound as a white solid. Yield: 37 mg (9%). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.59 (m, 2H), 7.43 (s, 1H), 7.39 (m, 2H), 7.24 (t, 1H, J=7.9 Hz), 6.91-6.87 (m, 2H), 6.81 (dd, 1H, J=7.9 Hz, J=2.1 Hz), 5.15 (s, 2H), 4.40 (m, 1H, J=2.8 Hz), 3.06 (m, 1H, J=6.5 Hz), 2.87 (m, 2H), 2.75-2.67 (m, 2H), 2.14 (m, 2H), 1.97 (s, 2H), 1.90 (m, 2H), 1.13 (d, 6H, J=6.6 Hz). 13C NMR (100 MHz, CDCl3) δ 177.0, 157.9, 157.7, 157.1, 151.6, 148.1, 137.5, 135.8, 131.7, 130.5, 129.9, 127.8, 123.3, 121.0, 120.7, 116.3, 115.5, 70.9, 55.3, 49.5, 44.4, 29.3, 23.3, 17.7. MS (ESI+) 494.0 (M+1H+).
