Water → N-((5-((2-acetamidopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydrofuran-3-carboxamide

Participants

Reaction Steps

A solution of Example B2 (0.104 g, 0.901 mmol) in DCE (3 mL) was treated with oxalyl chloride (0.079 mL, 0.901 mmol), stirred at RT for 1 h, then heated at 75° C. for 1 h. The mixture was cooled to RT, treated with a solution of Example A2 (0.11 g, 0.450 mmol) and TEA (0.188 mL, 1.351 mmol) in THF (4 mL) and stirred at RT for 1 h. The mixture was treated with water, extracted with 10% MeOH/DCM (1×), then DCM (1×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-((5-((2-acetamidopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydrofuran-3-carboxamide (42 mg, 24%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.98 (s, 2H), 10.56 (s, 1H), 8.24 (d, J=2.9 Hz, 1H), 8.18 (d, J=5.7 Hz, 1H), 8.08 (d, J=9.0 Hz, 1H), 7.72 (dd, J=9.0, 2.9 Hz, 1H), 7.64 (d, J=2.4 Hz, 1H), 6.69 (dd, J=5.7, 2.4 Hz, 1H), 3.87 (t, J=8.3 Hz, 1H), 3.76-3.75 (m, 2H), 3.67-3.66 (m, 1H), 3.28-3.26 (m, 1H), 2.08-2.06 (m, 2H), 2.03 (s, 3H); MS (ESI) m/z: 386.2 (M+H+).

Provenance & Evidence