Reaction Steps
A 0° C. solution of phosgene (15% in toluene, 2 mL, 2.84 mmol) in DCM (5 mL) was treated drop-wise with a solution of pyridine (0.1 mL, 1.236 mmol) and 5-methyl-1-(tetrahydro-2H-pyran-4-yl)imidazolidin-2-one (0.103 g, 0.561 mmol) in DCM (5 mL), stirred at RT for 1 h, then concentrated to dryness. The residue was dissolved in DCM (5 mL), cooled to 0° C., treated with a solution of Example A2 (0.10 g, 0.374 mmol) and pyridine (0.1 mL) in DCM (5 mL), warmed to RT and stirred overnight. The solids were removed via filtration, washed with DCM and the filtrate concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 4-methyl-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (16 mg, 9%). 1H NMR (400 MHz, DMSO-d6): δ 10.96 (s, 1 H), 8.36 (d, J=5.7 Hz, 1 H), 8.25 (s, 1 H), 8.23 (d, J=2.9 Hz, 1 H), 8.06 (d, J=9.0 Hz, 1 H), 7.95 (s, 1 H), 7.71 (dd, J=9.0, 2.9 Hz, 1 H), 7.22 (d, J=2.4 Hz, 1 H), 6.68 (dd, J=5.7, 2.4 Hz, 1 H), 3.90 (m, 4H), 3.87 (m, 1 H), 3.84 (s, 3 H), 3.66 (m, 1 H), 3.39 (m, 1 H), 3.34 (m, 1 H), 2.05 (m, 1 H), 1.90 (m, 1 H), 1.70 (m, 1 H), 1.68 (m, 1 H), 1.28 (d, J=5.4 Hz, 3H); MS (ESI) m/z: 478.2 (M+H+).
