1,4-Dioxane → 6-(6-Methylpyrazin-2-yl)-1-[6-(4-piperidyl)-2-pyridyl]pyrazolo[4,3-c]pyridine

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Reaction Steps

A mixture of tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylate; B; 110 mg; 0.2332 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 166 (13 mg) in 13% yield. 1H NMR (400 MHz, DMSO) δ 9.80 (s, 1H), 9.46 (s, 1H), 9.34 (s, 1H), 8.71 (s, 1H), 8.63 (s, 1H), 7.99 (t, J=7.9 Hz, 1H), 7.87 (d, J=8.1 Hz, 1H), 7.29 (d, J=7.5 Hz, 1H), 3.15 (d, J=12.0 Hz, 2H), 2.94 (tt, J=11.8, 3.5 Hz, 1H), 2.76-2.67 (m, 2H), 2.66 (s, 3H), 2.01 (d, J=12.1 Hz, 2H), 1.85 (qd, J=12.2, 3.8 Hz, 2H). MS (ESI) m/z: 372.2.

Provenance & Evidence