Hydrochloric Acid → 3-Butyl-6-(1-methyl-piperidin-4-yloxy)-4-[4-(pyridazin-3-ylmethoxy)-phenyl]-pyridazine trihydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-phenol (Example 19) (0.2 mmol, 69 mg) in dry DMF (1 mL) was added 3-bromomethyl-pyridazine (0.4 mmol, 70 mg), and potassium carbonate (0.4 mmol, 56 mg). And the mixture was stirred at 80° C. over night. It was then diluted with water/EtOAc. The organic layers were combined, dried, and condensed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% MeOH) to give a colorless sticky solid, which was dissolved in DCM (1.0 mL), 1N HCl in ether (1.0 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (77 mg). LCMS: m/z 435 [M+1]. 1H NMR (400 MHz, CD3OD): δ 7.81 and 7.88 (1 H, s), 7.46-7.51 (2 H, m), 7.30-7.41 (3 H, m), 7.20-7.25 (2 H, m), 5.37-5.53 (1 H, m), 5.20 (2 H, s), 3.30-3.53 (4 H, m), 3.12-3.17 (2 H, m), 2.93 (3 H, s), 2.08-2.58 (4 H, m), 1.44-1.53 (2 H, m), 1.24-1.34 (2 H, m), 0.81 (3 H, t).

Provenance & Evidence