7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one → HCID 46197770, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence