1,4-Dioxane → (3S)-1-[6-[6-(6-ethylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-3-amine

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Reaction Steps

A solution of (5)-tert-butyl(1-(6-(6-(6-ethylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-yl)carbamate (80 mg, 0.16 mmol) in hydrogen chloride (4 mol/l) in 1,4-dioxane (2.0 ml, 8.0 mmol) and 1,4-dioxane 2.0 mL was stirred at RT 18 h. The reaction was concentrated and submitted for reverse phase HPLC to give 156 (47 mg) in 50% yield. 1H NMR (400 MHz, DMSO) δ 9.55 (s, 1H), 9.49 (s, 1H), 9.33 (s, 1H), 8.66 (d, J=4.9 Hz, 2H), 7.75 (t, J=8.1 Hz, 1H), 7.21 (d, J=7.7 Hz, 1H), 6.82 (d, J=8.5 Hz, 1H), 4.42 (d, J=13.1 Hz, 1H), 4.12 (d, J=10.6 Hz, 1H), 3.17-3.06 (m, 1H), 2.93 (q, J=7.5 Hz, 2H), 2.88-2.71 (m, 2H), 1.84 (ddd, J=17.0, 13.4, 8.1 Hz, 2H), 1.58 (dd, J=24.7, 11.5 Hz, 1H), 1.35 (t, J=7.6 Hz, 3H). MS (ESI) m/z: 401.2.

Provenance & Evidence