Trifluoroacetic acid → HCID 57965053, compound

Participants

Reaction Steps

Trifluoroacetic acid (0.5 mL) was added to a solution of 4-[4-(2-methyl-pyridin-3-yloxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 92; 50 mg, 0.12 mmol) in dichloromethane (2 mL). The solution was stirred at room temperature for 30 min and then the solvents were evaporated, first using house vacuum and then high vacuum. Dichloromethane (4 mL) was added to the residue, and then phenyl chloroformate (23 μL, 0.18 mmol) was added, followed by triethylamine (110 μL, 0.8 mmol). The mixture was stirred overnight at room temperature and then water was added. The layers were separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid phenyl ester (8 mg, 15%) as an oil that changed to a waxy solid on standing. 1H NMR (300 MHz, CDCl3) δ 2.08-2.17 (m, 2H), 2.34-2.52 (m, 5H), 3.06-3.34 (m, 2H), 4.42-4.58 (m, 2H), 5.02-5.10 (m, 1H), 7.14 (d, 2H, J=7.9 Hz), 7.22-7.25 (m, 1H), 7.28-7.31 (m, 1H), 7.38 (t, 2H, J=7.7 Hz), 7.52 (d, 1H, J=8.1 Hz), 8.10 (s, 1H), 8.48-8.53 (m, 2H). Mass spectrum MH+=431. HRMS Calcd. For C23H23N6O3 (MH+): 431.1826. Found: 431.1825.

Provenance & Evidence