Pyridine → HCID 86268217, compound

Participants

Reaction Steps

A 0° C. solution of phosgene (15% in toluene, 2 mL, 2.84 mmol) in DCM (5 mL) was treated drop-wise with a solution of pyridine (0.1 mL, 1.236 mmol) and 1-methylimidazolidin-2-one (0.056 g, 0.561 mmol) in DCM (5 mL), stirred at RT for 2 h, then concentrated to dryness. The residue was dissolved in DCM (5 mL), cooled to 0° C., treated with a solution of Example A2 (0.10 g, 0.374 mmol) and pyridine (0.1 mL) in DCM (5 mL), warmed to RT and stirred for 4 h. The solids were removed via filtration, washed with DCM and the filtrate concentrated to dryness. The residue was treated with EtOAc/DCM/MeCN, allowed to stand overnight and the resulting solid collected via filtration to afford 3-methyl-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (80 mg, 52%). 1H NMR (400 MHz, DMSO-d6): δ 11.04 (s, 1 H), 8.66 (s, 1 H), 8.52 (d, J=6.7 Hz, 1 H), 8.35 (s, 1 H), 8.32 (m, 1 H), 8.12 (d, J=9.1 Hz, 1 H), 7.83 (dd, J=9.1, 2.9 Hz, 1 H), 7.64 (s, 1 H), 7.13 (m, 1 H), 3.90 (s, 3 H), 3.80 (m, 2 H), 3.45 (m, 2 H), 2.80 (s, 3H); MS (ESI) m/z: 394.2 (M+H+).

Provenance & Evidence