Ammonium Chloride → HCID 72714859, compound

Participants

Reaction Steps

To a solution of 1-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-3-(nitromethyl)azetidin-3-ol (100 mg, 0.25 mmol) in MeOH (5 mL) and H2O (0.5 mL) was added Zn powder (129 mg, 2 mmol) and NH4Cl (132 mg, 2.5 mmol). The reaction mixture was stirred at ambient temperature for 2 hours and filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to afford 270 as red solid (60 mg, 64.8%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.13 (s, 1H), 8.75 (s, 1H), 8.53 (s, 1H), 8.34-8.40 (m, 2H), 7.98 (s, 1H), 7.72-7.75 (m, 1H), 7.24-7.25 (m, 1H), 6.34-6.36 (d, J=8.5 Hz, 1H), 4.23-4.25 (d, J=8.5 Hz, 2H), 3.89-3.97 (m, 5H), 3.06-3.10 (m, 2H); MS (ESI) m/z: 377 [M+H]+.

Provenance & Evidence