1,2-Dimethoxyethane → N-[3-(3-{2-[(3-Chloro-4-{[2-(methyloxy)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide

Participants

Reaction Conditions

Reaction Steps

N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (0.1 g, 0.218 mmol) and 3-chloro-4-{[2-(methyloxy)ethyl]oxy}aniline (0.057 g, 0.283 mmol) were combined in a microwave safe reaction vessel. Ethylene glycol dimethyl ether (1.5 mL) and HCl (˜½ drop) were then added and the resulting mixture was heated in a microwave to 160° C. for 8 min. The reaction was then cooled to rt diluted with EtOAc (100 mL) and water (50 mL). The organic layer was separated, washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo onto silica gel. This was then purified via silica gel chromatography (EtOAc/Hexanes) to provide 55 mg of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 10.92 (s, 1H), 9.53 (s, 1H), 8.83 (d, 1H), 8.42 (br m, 1H), 8.25 (d, 1H), 8.00 (s, 1H), 7.93 (s, 1H), 7.80 (d, 1H), 7.62-7.42 (m, 4H), 7.33 (d, 1H), 7.24 (m, 2H), 7.12 (m, 1H), 7.03 (d, 1H), 6.52 (d, 1H), 4.11 (m, 2H), 3.65 (m, 2H), 3.30 (s, 3H); HRMS: calc. C33H26N6O3F2 (M+H)+ 627.1723 found 627.1732.

Provenance & Evidence