Pyridine → HCID 86269849, compound

Participants

Reaction Steps

A 0° C. solution of phosgene (15% in toluene, 2.82 mL, 4.00 mmol) in DCM (3 mL) was treated drop-wise with a solution of 1-methyl-2-imidazolidinone (0.107 g, 1.066 mmol) and pyridine (0.2 mL, 2.473 mmol) in DCM (3 mL), warmed to RT, stirred for 0.5 h, then concentrated to dryness. The residue was dissolved in DCM (3 mL), cooled to 0° C., treated with a solution of 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (0.15 g, 0.533 mmol) and DIEA (0.2 mL, 1.145 mmol) in DCM (3 mL), warmed to RT and stirred for 3 h. The mixture was treated with satd. NaHCO3, extracted with DCM (4×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN and the resulting solid was collected via filtration to afford 3-methyl-N-(4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (116 mg, 52%). 1H NMR (400 MHz, DMSO-d6): δ 10.90 (s, 1 H), 8.34 (d, J=5.7 Hz, 1 H), 8.25 (s, 1 H), 8.10 (s, 1 H), 8.01 (s, 1 H), 7.95 (s, 1 H), 7.16 (d, J=2.4 Hz, 1 H), 6.59 (dd, J=5.7, 2.5 Hz, 1 H), 3.84 (s, 3 H), 3.79-3.78 (m, 2 H), 3.45 (t, J=8.2 Hz, 2 H), 2.80 (s, 3 H), 2.14 (s, 3H); MS (ESI) m/z: 408.2 (M+H+).

Provenance & Evidence