Hydrochloric Acid → HCID 67371415, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(piperidin-4-yloxy)-pyridazine dihydrochloride (Example 14, 0.2 mmol, 97 mg) in EtOH (2 mL) was added 2-bromoethyl methyl ether (0.6 mmol, 57 μL), and potassium carbonate (0.6 mmol, 83 mg). The mixture was stirred at 60° C. for 3 hours, then cooled to room temperature, and filtered through celite. The celite cake was washed with DCM. The organic layers were combined and condensed in vacuo, and the residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH) to give a colorless sticky solid, which was dissolved in DCM (2 mL), 1N HCl in ether (2 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (52 mg). LCMS: m/z 469 [M+1]. 1H NMR (400 MHz, CD3OD): δ 7.31-7.40 (3 H, m), 7.06-7.10 (2 H, m), 5.38-5.57 (1 H, m), 4.39-4.44 (1 H, m), 3.53-3.78 (4 H, m), 3.43 (3 H, s), 3.25-3.42 (4 H, m), 2.96-3.02 (2 H, m), 2.04-2.55 (4 H, m), 1.97-2.02 (2 H, m), 1.78-1.83 (2 H, m), 1.29-1.62 (8 H, m), 1.22-1.30 (2 H, m), 0.80 (3 H, t).

Provenance & Evidence