Pyridine → 3,3-dimethyl-N-((6-methyl-5-((2-(3-methylisoxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)cyclobutanecarboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of Example B1 (0.028 g, 0.221 mmol) in DCE (4 mL) was treated with oxalyl chloride (0.019 mL, 0.221 mmol), heated at 83° C. for 2 h, cooled to RT, added drop-wise to a solution of Example A7 (0.052 g, 0.184 mmol) and pyridine (0.074 mL, 0.921 mmol) in THF (4.0 mL) and stirred at RT for 2 h. The mixture was treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over MgSO4 and concentrated to dryness. The resulting material was treated with MeCN and the solid collected via filtration and dried to afford 3,3-dimethyl-N-((6-methyl-5-((2-(3-methylisoxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)cyclobutanecarboxamide (51 mg, 64%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.08 (s, 1H), 10.70 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 7.92 (d, J 8.8 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H), 6.98-6.95 (m, 2H), 3.25 (m, 1H), 2.28 (s, 3H), 2.26 (s, 3H), 2.02-1.88 (m, 4H), 1.13 (s, 3H), 1.05 (s, 3H); MS (ESI) m/z: 436.2 (M+H+).

Provenance & Evidence