Triethylamine → HCID 66673596, compound

Participants

Reaction Steps

A mixture of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine trifluoroacetate (107 mg, 0.23 mmol), 5-bromo-3-(1-methylethyl)-1,2,4-thiadiazole (48 mg, 0.23 mmol), triethylamine (0.096 mL, 0.69 mol) and 1,2-dichloroethane (3 mL) was stirred and heated at reflux for 2 h, and the mixture was concentrated. The crude product was purified by reverse-phase preparative HPLC using CH3CN:H2O gradient (30:70 to 70:30) with 0.05% TFA as a modifier to give 25 mg (19%) of the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.49 (d, 1H, J=2.6 Hz), 8.13-8.06 (m, 2H), 8.06-7.99 (m, 2H), 7.76 (d, 1H, J=8.8 Hz), 7.39 (dd, 1H, Ja=8.8 Hz, Jb=2.6 Hz), 4.06-3.94 (m, 4H), 3.27-3.17 (m, 2H), 3.12-2.99 (m, 4H), 2.23-2.08 (m, 1H), 2.05-1.95 (m, 2H), 1.65-1.50 (m, 2H), 1.31 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 473 (M+H).

Provenance & Evidence