Phosgene (20% in toluene, 0.798 mL, 1.508 mmol) was treated drop-wise with a solution of Example B1 (0.128 g, 0.754 mmol) and pyridine (0.244 mL, 3.02 mmol) in DCM (5 mL), stirred at RT for 10 min, then concentrated to dryness. The residue was dissolved in DCM (5 mL), treated drop-wise with a solution of 2-fluoro-3-methyl-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)aniline (0.15 g, 0.503 mmol) and DIEA (0.527 mL, 3.02 mmol) in DCM (5 mL) stirred at RT for 3 h. The mixture was treated with satd. NaHCO3, extracted with DCM (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-(2-fluoro-3-methyl-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)phenyl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (0.188 g, 76%). 1H NMR (400 MHz, DMSO-d6): δ 10.76 (d, J=2.7 Hz, 1 H), 8.33 (d, J=5.7 Hz, 1 H), 8.24 (s, 1 H), 8.05 (t, J=9.0 Hz, 1 H), 7.95 (d, J=0.7 Hz, 1 H), 7.16 (d, J=2.4 Hz, 1 H), 6.98 (d, J=9.0 Hz, 1 H), 6.57 (dd, J=5.7, 2.4 Hz, 1 H), 3.93-3.83 (m, 6 H), 3.82-3.77 (m, 2 H), 3.46 (t, J=8.2 Hz, 2 H), 3.38 (dd, J=12.6, 10.8 Hz, 2 H), 2.05 (d, J=2.0 Hz, 3 H), 1.71 (m, 2 H), 1.59 (br d, J=12.3 Hz, 2H); MS (ESI) m/z: 495.2 (M+H+).
