Reaction Steps
Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (177 mg, 0.548 mmol) and 1-{3-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]phenyl}methanamine (140 mg, 0.603 mmol) were dissolved in MeOH (2 ml). The reaction was heated in a microwave at 120° C. for 30 minutes. The solvent was evaporated in vacuo. Purification by flash silica gel chromatography using a 40 g Biotage column with 100% EtOAc/MeOH/TEA 100:10:1 yielded the title compound as a white solid. Yield: 0.175 g (67%). 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.56 (m, 2H), 7.40 (s, 1H), 7.37 (m, 2H), 7.22 (t, 1H, J=7.9 Hz), 6.88 (d, 1H, J=7.9 Hz), 6.86 (m, 1H), 6.75 (dd, 1H, J=8.1 Hz, J=2.1 Hz), 5.15 (s, 2H), 4.33 (m, 1H), 3.24 (m, 1H), 2.97-2.88 (m, 1H), 2.86-2.69 (m, 4H), 2.08 (m, 1H), 1.99-1.88 (m, 1H), 1.70 (m, 1H), 1.57-1.47 (m, 1H), 1.34 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 158.3, 157.7, 157.1, 151.4, 148.2, 137.5, 135.7, 131.7, 130.4, 129.6, 127.8, 123.2, 121.0, 120.4, 115.8, 115.2, 73.6, 55.8, 49.5, 47.5, 46.8, 25.3, 24.6, 19.4. MS (ESI+) 478.00 (M+1H+).
