Water → HCID 90426070, compound

Participants

Reaction Steps

A 0° C. solution of Example C9 (0.350 g, 0.812 mmol) in DMF (5 mL) was treated with NaH (60% in mineral oil, 0.100 g, 2.50 mmol), stirred at RT for 0.5 h, treated with Example C4 (0.500 g, 1.836 mmol) and stirred at RT overnight. The mixture was treated with water, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-(5-chloro-2-fluoro-4-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)phenyl)-3-(3-methoxy-3-methylbutyl)-2-oxoimidazolidine-1-carboxamide (128 mg, 28%). 1H NMR (400 MHz, DMSO-d6): δ 10.90 (s, 1 H), 8.38 (m, 2 H), 8.26 (s, 1 H), 7.97 (d, J=0.7 Hz, 1 H), 7.57 (d, J=11.3 Hz, 1 H), 7.20 (d, J=2.5 Hz, 1 H), 6.64 (dd, J=5.7, 2.5 Hz, 1 H), 3.84 (s, 3H), 3.80 (m, 2 H), 3.48 (t, J=8.2 Hz, 2 H), 3.28 (m, 2 H), 3.09 (s, 3 H), 1.70 (m, 2 H), 1.11 (s, 6H); MS (ESI) m/z: (M+H+): 531.2.

Provenance & Evidence