Water → HCID 86270218, compound

Participants

Reaction Steps

A 0° C. mixture of Example A2 (0.160 g, 0.599 mmol) and pyridine (0.15 mL, 1.862 mmol) in DCM (5 mL) was treated with a solution of 3-(3-methoxypropyl)-2-oxoimidazolidine-1-carbonyl chloride (0.264 g, 1.197 mmol) in THF (5 mL), warmed to RT and stirred overnight. The mixture was treated with water, stirred for 10 min, the layers separated and the aqueous layer extracted with DCM (2×). The combined organics were dried over Na2SO4, concentrated to dryness, purified via silica gel chromatography (MeOH/DCM) and the resulting material was treated with Et2O and the solid collected via filtration to afford 3-(3-methoxypropyl)-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (155 mg, 57%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.97 (s, 1 H), 8.36 (d, J=5.7 Hz, 1 H), 8.25 (s, 1 H), 8.22 (d, J=2.9 Hz, 1 H), 8.07 (d, J=9.0 Hz, 1 H), 7.96 (s, 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), 3.84 (s, 3 H), 3.81-3.79 (m, 2 H), 3.46 (m, 2 H), 3.34 (m, 2 H), 3.27 (m, 2 H), 3.22 (s, 3 H), 1.77-1.69 (m, 2 H); MS (ESI) m/z: 452.2 (M+H+).

Provenance & Evidence