Pyridine → HCID 86268612, compound

Participants

Reaction Steps

A 0° C. solution of phosgene (15% in toluene, 1.37 mL, 1.948 mmol) in DCM (5 mL) was treated drop-wise with a solution of 2-(2-oxoimidazolidin-1-yl)acetonitrile (0.065 g, 0.519 mmol) and pyridine (0.2 mL, 2.473 mmol) in DCM (5 mL), warmed to RT, stirred 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 (0.069 g, 0.260 mmol) and pyridine (0.2 mL) in DCM (5 mL), warmed to RT and stirred for 3 h. The mixture was treated with satd. NaHCO3, extracted with DCM (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford 3-(cyanomethyl)-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (25 mg, 22%). 1H NMR (400 MHz, DMSO-d6): δ 10.69 (s, 1 H), 8.37 (d, J=5.7 Hz, 1 H), 8.25-8.24 (m, 2 H), 8.07 (d, J=9.0 Hz, 1 H), 7.96 (d, J=0.7 Hz, 1 H), 7.74 (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, 1H), 4.47 (s, 2 H), 3.93-3.84 (m, 5 H), 3.54 (t, J=8.2 Hz, 2H); MS (ESI) m/z: 419.2 (M+H+).

Provenance & Evidence