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

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (150 mg, 0.36 mmol) (see Example 1, Step C) in i-PrOH (4 mL) were added 3-{[2-(dimethylamino)ethyl]oxy}aniline (80 mg, 0.45 mmol) and 12 N HCl (3 drops). The reaction was stirred overnight at 80° C. The crude reaction mixture was diluted with DCM and extracted with saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered, and purified by column chromatography to generate the title compound in 84% yield. 1H NMR (400 MHz, d6-DMSO): δ 11.4 (bs, 1H), 9.58 (s, 1H), 8.85 (d, J=7.0 Hz, 1H), 8.50 (d, J=9.0 Hz, 1H), 8.28 (d, J=5.3 Hz, 1H), 8.00 (s, 1H), 7.83 (d, J=8.5 Hz, 1H), 7.45-7.57 (m, 4H), 7.28 (d, J=9.4 Hz, 1H), 7.10-7.15 (m, 2H), 6.51-6.56 (m, 2H), 4.00 (t, J=5.7 Hz, 2H), 2.7 (bs, 2H), 2.35 (s, 6H). ES-LC/MS m/z=562 [M+H]+.

Provenance & Evidence