Triethylamine → HCID 23091632, compound

Participants

Reaction Steps

Ethanesulfonyl chloride (26 μL, 0.28 mmol) was added dropwise to a solution of triethylamine (35 μL, 0.25 mmol) and N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)ethanamine (78 mg, 0.23 mmol) in dichloromethane (0.5 mL) at 0° C. allowed to warm to ambient temperature and stirred overnight. The reaction was quenched with NaHCO3 (10 mL), extracted using dichloromethane (3×10 mL), dried using Na2SO4 and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, 96.5:3.5:0.35 to 95:5:0.5 to give the title compound as a pale brown oil (55 mg, 54%). 1H NMR (400 MHz, CDCl3) δ 7.24 (d, 2H), 6.90 (d, 2H), 4.02 (t, 2H), 3.84-3.72 (m, 2H), 3.48 (t, 2H), 3.32 (s, 2H), 2.76 (quartet, 2H), 2.72-2.60 (m, 4H), 2.60-2.48 (m, 4H), 2.20-2.08 (m, 2H), 2.04 (pentet, 2H), 1.98-1.90 (m, 2H), 1.86-1.76 (m, 4H), 1.30 (t, 3H), 0.88 (t, 3H). HRMS (ESI+) 439.2625 (M+H)+.

Provenance & Evidence