Phosgene (15% in toluene, 1.75 mL, 2.449 mmol) was treated with a solution of (R)-1-(1-methoxypropan-2-yl)imidazolidin-2-one (155 mg, 0.980 mmol) and pyridine (116 mg, 1.470 mmol) in DCM (2 mL), stirred at RT for 15 min, then concentrated to dryness. The residue was dissolved in DCM (2 mL), treated with a solution of Example A2 (131 mg, 0.490 mmol) and TEA (248 mg, 2.449 mmol) in DCM (2 mL) and stirred at RT for 4 h. The mixture was treated with EtOAc, washed with satd. NaHCO3, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford (R)-3-(1-methoxypropan-2-yl)-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (38 mg, 17%). 1H NMR (400 MHz, DMSO-d6): δ 10.98 (s, 1 H), 8.37 (d, J=5.7 Hz, 1 H), 8.25 (s, 1 H), 8.22-8.21 (m, 1 H), 8.06-8.05 (m, 1 H), 7.95 (d, J=0.7 Hz, 1 H), 7.72 (dd, J=9.0, 2.9 Hz, 1 H), 7.22 (d, J=2.4 Hz, 1 H), 6.69 (dd, J=5.7, 2.4 Hz, 1 H), 4.10-4.09 (m, 1 H), 3.84 (s, 3 H), 3.81-3.79 (m, 2 H), 3.40-3.39 (m, 4 H), 3.26 (s, 3 H), 1.09 (d, J=6.9 Hz, 3H); MS (ESI) m/z: 452.2 (M+H+).
