Glycolic Acid → HCID 57524790, compound

Participants

Reaction Steps

To a solution of 3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)propan-1-amine (200 mg, 0.458 mmol), glycolic acid (52 mg, 0.687 mmol) and DIPEA (178 mg, 1.37 mmol) in DMF (5 mL), TBTU (191 mg, 0.596 mmol) is added. The mixture is stirred at rt for 18 h before it is diluted with EA (50 mL) and washed twice with sat. aq. NaHCO3 solution (50 mL) followed by brine (50 mL). The org. extract is dried over Na2SO4, filtered, and concentrated. The crude product is purified by prep. HPLC to give the title compound (116 mg) as a pale yellow oil; LC-MS: tR=1.14 min, [M+H]+=495.25; 1H NMR (CD3OD): δ 7.85 (s, 1H), 7.83 (s, 1H), 7.53 (s, 1H), 7.28 (s, 1H), 4.01 (s, 2H), 4.00 (s, 3H), 3.94 (t, J=6.1 Hz, 2H), 3.57 (t, J=6.9 Hz, 2H), 3.24-3.31 (m, 1H), 2.77 (q, J=7.6 Hz, 2H), 2.38 (s, 3H), 2.05-2.16 (m, 4H), 1.86-1.96 (m, 4H), 1.72-1.82 (m, 2H), 1.31 (t, J=7.5 Hz, 3H).

Provenance & Evidence