Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

To the flask containing N-(2-(5-chloro-2-fluorophenyl)-5-methylpyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(2-(5-chloro-2-fluorophenyl)-5-methylpyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine (0.561, 1.184) was added TFA (5.9 mL) and the mixture was stirred at 70° C. for 3 hours. The reaction was cooled to room temperature and concentrated under vacuum to a dark amber residue. To this residue was combined with dichloromethane (25 mL) and saturated sodium carbonate solution (25 mL) resulting in a precipitate which was filtered, rinsed with dichloromethane and water and dissolved in EtOAc, then extracted with water and saturated sodium bicarbonate The organic layer was separated, dried over sodium sulfate, and concentrated to give a yellow solid that was purified by preparative HPLC using a Sunfire Prep 5 μm C18, 75×30 mm column eluting with a gradient of 18-25% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) to give the title compound as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.30-2.40 (m, 3H) 7.42 (dd, J=10.86, 8.84 Hz, 1H) 7.53-7.67 (m, 1H) 7.79 (br. s., 1H) 7.94-8.04 (m, 1H) 8.46 (d, J=5.81 Hz, 1H) 8.76 (s, 1H). MS [M+H] found 354.2.

Provenance & Evidence