Reaction Steps
Method H1 (in Pyridine). 7-(4-Aminophenoxy)-2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyridine (65 mg, 0.27 mmol) was suspended in dry pyridine (3 mL) and heated at 50° C. Phenyl isocyanate (30 μL, 0.28 mmol) was added; the solution became clear. The reaction mixture was heated at reflux for 2 hours, then it was allowed to cool at room temperature. DCM (20 mL) was added, the precipitate formed was recovered by filtration and washed with more DCM, to afford 1-(4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyridin-7-yl-oxy)phenyl)-3-phenyl-urea (67 mg, 69%). 1H-NMR (δ, ppm, DMSO-d6): 6.34 (d, 1H, HPy,5, J=7.5 Hz), 6.98 (t, 1H, Harom,Ph′,4, J=7.5 Hz), 7.13 (d, 2H, Harom,Ph,3+5, J=8.75 Hz), 7.29 (t, 2H, Harom,Ph′,3+5), 7.46 (d, 2H, Harom,Ph′,2+6), 7.53 (d, 2H, Harom,Ph,2+6), 7.76 (d, 1H, HPy,6) 8.67 (s, 1H, NHurea,1), 8.76 (s, 1H, NHurea,3), 11.19 (s, 1H, NHPy3), 11.35 (s, 1H, NHPy2). LC-MS (m/z): 362 (M+H, 100).
