Pyridine → HCID 86270403, compound

Participants

Reaction Conditions

Reaction Steps

A 0° C. solution of phosgene (20% in toluene, 0.092 mL, 0.174 mmol) in DCM (2 mL) was treated slowly with a solution of Example B6 (26 mg, 0.166 mmol) and pyridine (0.027 mL, 0.331 mmol) in DCM (2 mL), stirred at 0° C. for 0.5 h, then concentrated to dryness. The residue was dissolved in DCM (2 mL), treated with pyridine (0.0400 mL, 0.495 mmol), cooled to 0° C., treated slowly with a solution of Example A2 (36 mg, 0.165 mmol) in DCM (2 mL), warmed to RT and stirred for 1.5 h. The mixture was diluted with water, extracted with DCM and the organic layer was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford (S)—N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydrofuran-3-yl)imidazolidine-1-carboxamide (33 mg, 45%). 1H NMR (400 MHz, DMSO-d6): δ 10.95 (s, 1 H), 8.38 (d, J=5.8 Hz, 1 H), 8.27 (s, 1 H), 8.23 (d, J=2.9 Hz, 1 H), 8.07 (d, J=9.0 Hz, 1 H), 7.97 (s, 1 H), 7.72 (dd, J=9.0, 2.9 Hz, 1 H), 7.25 (s, 1 H), 6.71 (d, J=5.5 Hz, 1 H), 4.57-4.49 (m, 1 H), 3.91-3.86 (m, 1 H), 3.84 (s, 3 H), 3.83-3.76 (m, 3 H), 3.70-3.57 (m, 2 H), 3.51-3.43 (m, 2 H), 2.19-2.09 (m, 1 H), 2.02-1.91 (m, 1 H); MS (ESI) m/z: 450.1 (M+H+).

Provenance & Evidence