Reaktion #1951837

Reaktionsgleichung

phenyl 3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl-carbamate

7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

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title compound

Ausbeute 86.4%

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

Ausbeute 86.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONcontaining 4 Angstrom molecular sieves
2. 2
   FiltrationAfter dilution with EtOAc (10 mL) and filtration
3. 3
   Sonstigeto remove the molecular sieves
4. 4
   Waschenthe solution was washed with 0.5 M citric acid (aqueous), saturated NaHCO3 (aqueous) and brine
5. 5
   TrocknenThe organic layer was dried over MgSO4
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   WaschenThe orange solid residue was washed with Et2O

Vorschrift

Method I1. A mixture of phenyl 3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl-carbamate (66 mg, 0.18 mmol) and 7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one (30 mg, 0.12 mmol) in anhydrous THF (1.5 mL) containing 4 Angstrom molecular sieves was heated at 50° C. for 14 hours. After dilution with EtOAc (10 mL) and filtration to remove the molecular sieves, the solution was washed with 0.5 M citric acid (aqueous), saturated NaHCO3 (aqueous) and brine. The organic layer was dried over MgSO4 and the solvent was evaporated under reduced pressure. The orange solid residue was washed with Et2O to afford the title compound (52 mg, 85%) as a slightly orange solid. 1H-NMR (6, ppm, DMSO-d6): 1.28 (s, 9H, t-Bu), 6.31 (d, 1H, HPy,5, J=6.0 Hz), 6.35 (s, 1H, HPyz,4), 7.09 (d, 2H, Harom,Ph,3+5, J=8.9 Hz), 7.37 (t, 2H, Harom,4-F-Ph,3+5 J=8.8 Hz), 7.47 (d, 2H, Harom,Ph,2+6, J=8.9 Hz), 7.57 (dd, 2H, Harom,4-F-Ph,2+6 J=8.8 Hz and J=5.0 Hz), 7.74 (d, 1H, HPy,6, J=6.0 Hz), 8.37 (bs, 1H, NHurea), 9.06 (bs, 1H, NHurea), 11.16 (bs, 1H, NHPy3) 11.34 (bs, 1H, NHPy2). LC-MS (m/z): 502 (M+H, 100).

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