Pyridine → 3,3-dimethyl-N-((5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-yl)carbamoyl)cyclobutanecarboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of Example B1 (0.120 g, 0.944 mmol) in dioxane (10 mL) was treated with oxalyl chloride (0.120 g, 0.945 mmol), heated at 100° C. for 3 h, concentrated to dryness, dissolved in DCM (10 mL), added to a solution of 5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-amine (0.120 g, 0.447 mmol) in DCM (10 mL) and pyridine (0.070 g, 0.885 mmol) and stirred at RT overnight. The mixture was concentrated to dryness treated with MeCN and the solid collected via filtration and dried to afford 3,3-dimethyl-N-((5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-yl)carbamoyl)cyclobutanecarboxamide (95 mg, 49%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.07 (s, 1H), 10.71 (s, 1H), 8.63 (s, 1H), 8.47 (s, 1H), 8.26 (d, J=2.8 Hz, 1H), 8.16 (s, 1H), 8.05 (d, J=9.0 Hz, 1H), 7.75 (dd, J=9.0, 2.8 Hz, 1H), 7.43 (s, 1H), 3.89 (s, 3H), 3.30 (m, 1H), 2.00 (m, 4H), 1.13 (s, 3H), 1.05 (s, 3H); MS (ESI) m/z: 422.2 (M+H+).

Provenance & Evidence