Pyridine → 2-methoxy-N-((5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)acetamide

Participants

Reaction Steps

A suspension of Example B6 (0.060 g, 0.673 mmol) in DCE (4 mL) was treated with oxalyl chloride (0.059 mL, 0.673 mmol), stirred at RT for 1 h, then heated to 80° C. for 1.5 h. The mixture was cooled to RT, added drop-wise to a solution of Example A2 (0.15 g, 0.561 mmol) and pyridine (0.226 mL, 2.81 mmol) in THF (4 mL) and stirred at RT overnight. The mixture was treated with satd. Na2CO3, extracted with EtOAc (4×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN, sonicated and the resulting solid collected via filtration to afford 2-methoxy-N-((5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)acetamide (186 mg, 87%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.78 (s, 1H), 10.71 (s, 1H), 8.37 (d, J=5.7 Hz, 1H), 8.27 (d, J=2.9 Hz, 1H), 8.26 (s, 1H), 8.03 (m, 1H), 7.96 (d, J=0.7 Hz, 1H), 7.74 (dd, J=9.0, 2.9 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 6.71 (dd, J=5.7, 2.4 Hz, 1H), 4.11 (s, 2H), 3.84 (s, 3H), 3.34 (s, 3H); MS (ESI) m/z: 383.1 (M+H+).

Provenance & Evidence