Hydrochloric Acid → 1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridine

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Reaction Steps

A suspension of tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (320 mg, 0.68 mmol) in a solution of HCl in MeOH (3.0 N, 20 mL) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by prepared HPLC to afford 175 as a light yellow solid (220 mg, yield 87%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.43 (s, 1H), 9.39 (s, 1H), 9.35 (d, J=3.0 Hz, 1H), 9.28 (d, J=3.0 Hz, 1H), 9.06 (d, J=11.5 Hz, 1H), 8.66 (d, J=5.5 Hz, 1H), 7.70 (dd, J=8.0 and 16.5 Hz, 1H), 7.17 (dd, J=7.5 and 11.0 Hz, 1H), 6.61 (t, J=8.0 Hz, 1H), 3.83 (s, 2H), 3.77 (s, 2H), 3.56 (m, 1H), 2.95 (t, J=5.0 Hz, 2H), 2.70 (t, J=6.0 Hz, 2H), 1.84 (t, J=5.0 Hz, 2H). ESI (MS) m/z: 373 [M+1]+.

Provenance & Evidence