Hydrochloric Acid → (S)-1-(3-chloro-6-(6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amine

Participants

Reaction Steps

To a solution of tert-butyl N-[(3S)-1-[3-chloro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (0.140 mmol; 72.7 mg) in Methanol (5 mL) was added hydrochloric acid, 4.0 M in 1,4-Dioxane (5 mL). The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 176 as an off-white solid (23.3 mg, 40%). 1H NMR (400 MHz, DMSO) δ 9.67-9.61 (s, 1H), 9.47-9.42 (s, 1H), 9.34-9.28 (s, 1H), 8.71-8.67 (s, 1H), 8.64-8.61 (s, 1H), 8.01-7.94 (d, J=8.4 Hz, 1H), 7.57-7.51 (d, J=8.4 Hz, 1H), 3.91-3.83 (d, J=8.8 Hz, 1H), 3.81-3.72 (d, J=12.3 Hz, 1H), 3.25-3.19 (m, 1H), 2.97-2.89 (m, 1H), 2.77-2.71 (dd, J=11.9, 9.1 Hz, 1H), 2.67-2.62 (d, J=8.6 Hz, 3H), 1.98-1.87 (dd, J=16.2, 6.5 Hz, 2H), 1.84-1.40 (dd, J=32.9, 22.1 Hz, 3H), 1.36-1.23 (td, J=13.5, 4.6 Hz, 1H); MS (ESI) m/z: 421.1 [M+H]+

Provenance & Evidence