3-[2-(Dimethylamino)ethoxy]aniline → N-[3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}-4-fluoropyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide

Participants

Reaction Steps

To the solution of N-{3-[3-(2-chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (0.09 g) in isopropanol (5 mL) was added 3-{[2-(dimethylamino)ethyl]oxy}aniline (0.07 g) and 3 drops of concentrated hydrochloric acid. The reaction was microwaved in a sealed tube at 180° C. for 10 min. The isopropanol was removed by rotaevaporation and the residue was treated with sat. NaHCO3 (5 mL), extracted with EtOAc (2×5 mL), and dried (Na2SO4). Concentration and purification with column chromatography afforded the title compound as a yellow solid (0.11 g, 93% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.30 (d, J=2.7 Hz, 6H), 2.70 (t, J=5.7 Hz, 2H), 4.01-4.07 (m, 2H), 6.58-6.68 (m, 2H), 6.95-7.03 (m, 2H), 7.10 (d, J=7.9 Hz, 1H), 7.17-7.30 (m, 4H), 7.37-7.50 (m, 4H), 7.80 (s, 1H), 7.93 (d, J=7.9 Hz, 1H), 8.20 (dd, J=5.2, 2.8 Hz, 1H), 8.39-8.48 (m, 2H); ESIMS (M+H)+=624.

Provenance & Evidence