Hydrochloric Acid → Diethylammonium

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 1-(3-fluoro-4-(5-(pyridin-2-ylmethyl)benzofuran-2-yl)benzyl)azetidine-3-carboxylate (31 mg, 70 μmol) in THF (2 mL) was treated with 1M LiOH in H2O (0.4 mL) and stirred at 24° C. for 3 h, neutralized with 0.1M aqueous HCl, and evaporated. Purification by SFC (supercritical flash chromatography) resulted in title compound as its diethylammonium salt [hS1P1 EC50=31 nM]. 1H NMR (400 MHz, CD3OD) δ ppm 8.48 (d, J=0.8 Hz, 1H), 8.02 (t, J=7.9 Hz, 1H), 7.78 (t, J=5.9 Hz, 1H), 7.54 (s, 1H), 7.48 (d, J=10.0 Hz, 1H), 7.33-7.22 (m, 6H), 4.25 (s, 2H), 3.95 (s, 2H), 3.82 (t, J=8.6 Hz, 2H), 3.68 (t, J=8.5 Hz, 2H), 3.36-3.34 (m, 1H, partially overlapping with CD3OH signal), 3.05 (q, J=7.4 Hz, 2H), 1.31 (t, J=7.2 Hz, 3H). MS (ESI) m/z: Calculated: 416.2; Observed: 417.2 (M++1).

Provenance & Evidence