Reaction Steps
2-(4-Chlorophenyl)-6-(3-hydroxybenzyl)thieno[2,3-d]pyridazin-7(6H)-one (0.082 g, 0.22 mmol), 1-methylpiperidin-4-ol (0.050 g, 0.43 mmol) and TPP (0.107 g, 0.41 mmol) were stirred in THF (3 mL) at 0° C. DEAD (0.2 mL, 40% in toluene, 0.44 mmol) was added and the resulting mixture was allowed to attain room temperature and the stirring was continued over night. Concentration and purification on C8-HPLC (0.1% HOAc, gradient 30→40% CH3CN) gave 0.019 g (16%) of the title compound. 1H NMR (400 MHz, CDCl3/MeOH-d4 1:1, internal standard: MeOH-d4) δ 8.30 (s, 1H), 7.66 (d, 2H, J=8.5 Hz), 7.59 (s, 1H), 7.43 (d, 2H, J=8.5 Hz), 7.22 (t, 1H, J=7.9 Hz), 7.03 (m, 2H), 6.83 (d, 1H, J=7.7 Hz), 5.39 (s, 2H), 4.53 (br, 1H), 3.07-2.86 (m, 4H), 2.59 (s, 3H), 2.16-1.94 (m, 4H), 1.97 (s, 3H). 13C NMR (100 MHz, CDCl3/MeOH-d4 1:1, internal standard: MeOH-d4) δ 177.1, 157.9, 157.5, 153.2, 141.2, 138.8, 136.5, 136.3, 134.7, 131.6, 130.4, 130.1, 128.6, 122.1, 119.9, 116.8, 115.8, 69.1, 51.1, 44.4, 28.8, 22.3. MS (ESI+) 466.1 (M+1H+).
