Trifluoroacetic acid → HCID 178494163, compound

Participants

Reaction Steps

To a stirred solution of (R)-3-{6-[2-tert-butoxycarbonyl-5-(2-methoxy-6-methyl-pyridin-3-yl)-2H-pyrazol-3-ylamino]-pyrazin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (13.0 g, 22.3 mmol) in dichloromethane (150 mL) is added a solution of trifluoroacetic acid (12.4 mL, 167 mmol) dichloromethane (20 mL) over a period of 5 min at 0° C. The reaction is allowed to warm to room temperature and stirred for 3 h. The reaction is diluted with dichloromethane (1000 mL), followed by addition of saturated sodium bicarbonate solution (250 mL) and then stirred for 4 h. The organic portion is separated and dried over anhydrous sodium sulfate, filtered, and evaporated. The resulting material is crystallized from isopropanol to obtain the desired product. Yield=7.2 g (85%). 1H NMR (400 MHz, DMSO-d6) δ 12.40 (s, 1H), 9.71 (s, 1H), 8.02 (d, J=7.6 Hz, 1H), 7.97 (s, 1H), 7.46)(s, 1H), 6.93 (d, J=7.6 Hz, 1H), 6.91 (s, 1H), 4.94-4.86 (m, 1H), 3.97 (s, 3H), 3.20-3.13 (m, 1H), 2.83-2.75 (m, 1H), 2.57 (dd, J=12.0, 84 Hz, 1H), 2.53-2.45 (m obscured, 1H), 2.42 (s, 3H), 2.15-2.05 (m, 1H), 1.71-1.63 (m, 1H), 1.60-1.49 (m, 1H), 1.49-1.40 (m, 1H); ES/MS m/z 382.5 [M+H]+.

Provenance & Evidence