Pyridine → US9133183, Example 15

Participants

Reaction Steps

A solution of Example B7 (0.085 g, 0.505 mmol) and pyridine (0.133 g, 1.684 mmol) in DCM (2 mL) was added to phosgene (20% in toluene, 0.833 g, 1.684 mmol), under Ar, stirred for 15 min, then concentrated to dryness. The residue was dissolved in DCM (2 mL), treated with a solution of Example A2 (0.09 g, 0.337 mmol) and TEA (0.102 g, 1.010 mmol) in DCM (2 mL) and stirred at RT for 1 h. The mixture was treated with water, extracted with DCM (2×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 3-cyclohexyl-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (100 mg, 64%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.99 (s, 1 H), 8.37 (d, J=5.7 Hz, 1 H), 8.26 (s, 1 H), 8.23 (d, J=2.9 Hz, 1 H), 8.07 (d, J=9.0 Hz, 1 H), 7.96 (s, 1 H), 7.71 (dd, J=9.0, 2.9 Hz, 1 H), 7.23 (d, J=2.4 Hz, 1 H), 6.70 (dd, J=5.7, 2.4 Hz, 1 H), 3.84 (s, 3 H), 3.79 (m, 2 H), 3.61 (m, 1 H), 3.43 (m, 2 H), 1.67 (m, 5 H), 1.35 (m, 4 H), 1.08 (m, 1 H); MS (ESI) m/z: 462.2 (M+H+).

Provenance & Evidence