Ethyl Acetate → N-{3-tert-Butyl-1-[4-(2-methoxyethoxy)phenyl]-1H-pyrazol-5-yl}-N'-[4-(pyridin-4-yloxy)-phenyl]urea

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-tert-butyl-2-[4-(2-methoxyethoxy)phenyl]2H-pyrazol-3-ylamine (75 mg, 0.26 mmol) in anhydrous DCE (1.0 mL) was added CDT (37 mg, 0.31 mmol), and the reaction mixture was stirred at 60° C. for 6 h. A solution of 4-(pyridin-4-yloxy)phenylamine (48 mg, 0.26 mmol) in DCE (1.3 mL) was then added, and the mixture was stirred at 60° C. for 20 h. The reaction mixture was diluted into EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated at reduced pressure. The crude product was purified by HPLC and recrystallized from ether/DCM/hexane to give 45.2 mg (35%) of the title compound as a white solid. 1H-NMR (DMSO-d6) δ 9.01 (s, 1H), 8.39 (d, J=4.8 Hz, 2H), 8.28 (s, 1H), 7.46 (d, J=8.4 Hz, 2H), 7.38 (d, J=8.7 Hz, 2H), 7.05 (d, J=8.7 Hz, 4H), 6.84 (d, J=4.8 Hz, 2H), 6.29 (s, 1H), 4.14 to 4.10 (m, 2H), 3.66 to 3.63 (m, 2H), 3.28 (s, 3H), 1.23 (s, 9H); MS LC-MS [M+H]+=502, RT=2.80 min.

Provenance & Evidence