Methyl iodide → HCID 66673526, compound

Participants

Reaction Steps

Iodomethane (0.004 mL, 0.07 mmol) was added to a solution of 4′-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-N-[2-(4-morpholinyl)ethyl]-4-biphenylsulfonamide trifluoroacetate (Example 109, 46 mg, 0.07 mmol) and KOH (12 mg, 0.21 mmol) in EtOH (1 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The mixture was charged with additional iodomethane (0.006 mL, 0.11 mmol), and stirred at ambient temperature overnight. The mixture was charged with additional iodomethane (0.006 mL, 0.11 mmol) and stirred at ambient temperature overnight. The mixture was quenched with MeOH and concentrated. The crude product was purified by reverse-phase preparative HPLC using a CH3CN:H2O gradient (0.5:99.5 to 90:10) with 0.05% TFA as a modifier to give 19 mg (39%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.80-7.75 (m, 2H), 7.71-7.66 (m, 2H), 7.52 (d, 2H, J=8.8 Hz), 6.97 (d, 2H, J=8.8 Hz), 4.25-4.15 (m, 2H), 4.07-3.83 (m, 6H), 3.78-3.55 (m, 3H), 3.51-3.32 (m, 4H), 3.17-2.97 (m, 3H), 2.95-2.85 (m, 1H), 2.80 (s, 3H), 2.14-2.02 (m, 1H), 2.01-1.91 (m, 2H), 1.54-1.39 (m, 2H), 1.27 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 584 (M+H).

Provenance & Evidence