Pyridine → HCID 90426325, compound

Participants

Reaction Steps

A solution of Example B1 (141 mg, 0.826 mmol) and pyridine (98 mg, 1.239 mmol) in DCM (4 mL) was added to phosgene (20% in toluene, 1.021 g, 2.065 mmol), under Ar, stirred for 15 minutes, then concentrated to dryness. The residue was treated with a solution of 5-bromo-2-fluoro-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)aniline (150 mg, 0.413 mmol) and TEA (209 mg, 2.065 mmol) in DCM (4 mL) and stirred at RT for 0.5 h. The mixture was diluted with water, extracted with EtOAc (2×) and combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford N-(5-bromo-2-fluoro-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)phenyl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (134 mg, 58%). 1H NMR (400 MHz, DMSO-d6): δ 10.90 (d, J=2.7 Hz, 1 H), 8.54 (d, J=8.2 Hz, 1 H), 8.36 (d, J=5.7 Hz, 1 H), 8.26 (s, 1 H), 7.97 (s, 1 H), 7.55 (d, J=11.3 Hz, 1 H), 7.19 (d, J=2.4 Hz, 1 H), 6.61 (dd, J=5.7, 2.5 Hz, 1 H), 3.93-3.87 (m, 3 H), 3.84 (s, 3 H), 3.83-3.78 (m, 2 H), 3.47 (m, 2 H), 3.37 (m, 2 H), 1.71 (m, 2 H), 1.59 (m, 2H); MS (ESI) m/z: (M+H+): 559.1.

Provenance & Evidence