Reaktion #1951823

Reaktionsgleichung

7-(4-Aminophenoxy)-2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyridine

Phenyl isocyanate

DCM

→

1-(4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyridin-7-yl-oxy)phenyl)-3-phenyl-urea

Ausbeute 69.0%

Lösungsmittel

Pyridine

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturat reflux for 2 hours
3. 3
   Temperaturto cool at room temperature
4. 4
   Sonstigethe precipitate formed
5. 5
   Filtrationwas recovered by filtration
6. 6
   Waschenwashed with more DCM

Vorschrift

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).

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