Hydrochloric Acid → HCID 67372434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{4-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-phenoxymethyl}-cyclohexanecarboxylic acid (0.2 mmol, 97 mg) in DMF (1 mL) was added dimethylamine hydrochloride (0.3 mmol, 25 mg), HBTU (0.4 mmol, 152 mg), DIEA (0.4 mmol, 70 μL). The mixture was stirred at 100° C. for 2 hours. The mixture was then diluted with water/EtOAc and neutralized with acetic acid. The organic layers were combined, dried, and condensed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% in MeOH) to give a colorless sticky solid, which was dissolved in DCM (1 mL), 2N HCl in ether (1 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (89 mg). LCMS: m/z 510 [M+1]. 1H NMR (400 MHz, CD3OD): δ 7.64 and 7.76 (1 H, s), 7.45-7.51 (2 H, m), 7.13-7.17 (2 H, m), 5.37-5.54 (1 H, m), 4.30 (2 H, d), 3.35-3.69 (3 H, m), 3.08-3.30 (4 H, m), 2.94 (3 H, s), 2.81 (6 H, s), 2.21-2.74 (5 H, m), 1.86-2.98 (2 H, m), 1.25-1.54 (10 H, m), 0.82 (3 H, t).

Provenance & Evidence