Ethyl Acetate → N-Methyl-N-[2-(2-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-ethyl)-phenyl]-methanesulfonamide

Participants

Reaction Steps

To a Paar bottle was added N-methyl-N-(2-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl}-phenyl)-methanesulfonamide (50.0 mg, 0.0970 mmol), 10% palladium on carbon (50% wet) (25.0 mg, 0.0117 mmol) and 2:1 ethyl acetate:methanol (10 mL). The mixture was degassed and charged with hydrogen (38 psi). The mixture was shaken on a Paar apparatus for 1 hour. The mixture was degassed and kept under an atmosphere of Nitrogen. The mixture was filtered through a plug of diatomaceous earth and rinsed with dichloromethane. The filtrate was evaporated. N-Methyl-N-[2-(2-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-ethyl)-phenyl]-methanesulfonamide was isolated as a pale yellow foam (0.037 g, 73%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.31 (s, 1H), 8.58 (d, J=6.6 Hz, 1H), 7.55 (d, J=7.8 Hz, 2H), 7.48-7.44 (m, 1H), 7.35-7.26 (m, 3H), 7.23 (d, J=7.0 Hz, 1H), 6.92-6.84 (m, 3H), 3.23-3.00 (m, 14H), 2.48-2.43 (m, 4H), 2.22 (s, 3H). MS=520 (MH)+.

Provenance & Evidence