tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate → 1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

Participants

Reaction Steps

A solution of tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]-pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (200 mg, 0.39 mmol) in HCl/MeOH (2M, 10 mL) was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The crude was purified by reverse phase preparative HPLC to afford 161 as a yellow solid (70 mg, 43.5%). 1H NMR (500 MHz, CDCl3) δ (ppm) 9.055-9.057 (d, J=1 Hz, 1H), 8.74 (s, 1H), 8.23 (s, 1H), 8.17 (s, 1H), 7.97 (s, 1H), 7.60-7.63 (t, J=16 Hz, 1H), 7.28 (s, 1H), 6.41-6.43 (d, J=8 Hz, 1H), 4.04-4.06 (d, J=7 Hz, 2H), 3.89-3.94 (m, 4H), 3.17-3.19 (t, J=11 Hz, 2H), 2.91-2.93 (t, J=11.5 Hz, 2H), 2.03-2.06 (t, J=12.5 Hz, 2H), 1.35-1.36 (m, 1H), 0.69-0.73 (m, 2H), 0.43-0.46 (m, 2H); MS (ESI) m/z: 415 [M+H]+.

Provenance & Evidence