반응 #1951837

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

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

→

title compound

수율 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

수율 86.4%

용매

THF

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후처리

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

실험 절차

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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