Ethanol → HCID 67287710, compound

Participants

Reaction Steps

Ethyl 6-chloro-7-(4-(2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylate (133 mg, 0.241 mmol) was diluted with tetrahydrofuran (2 mL) followed by the addition of aqueous NaOH (603 μL, 1.21 mmol) and ethanol (1 mL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 2N aqueous HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 6-chloro-7-(4-(2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid (70 mg, 0.134 mmol, 55.5% yield). MS (es+apci, positive) m/z=523.2. 1H NMR (400 MHz, CDCl3) δ 7.71 (d, 2H), 7.42 (s, 1H), 7.35 (d, 1H), 6.96 (d, 2H), 6.54 (s, 1H), 6.47 (d, 1H), 4.25 (dd, 2H), 3.74 (t, 1H), 3.68 (t, 2H), 3.02 (t, 2H), 2.38-2.32 (m, 1H), 2.19-2.08 (m, 2H), 1.13-1.09 (m, 2H), 0.93-0.89 (m, 2H).

Provenance & Evidence