Ammonium formate → HCID 90410008, compound

Participants

Reaction Steps

To a stirring solution of 4-benzyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperazine-1-carboxamide (0.574 g, 1.321 mmol) in MeOH/THF (1:1, 30 mL) at RT was sequentially added ammonium formate (0.833 g, 13.21 mmol) and zinc powder (0.864 g, 13.21 mmol). The resulting suspension was stirred briskly at RT. After 75 min, the reaction was filtered through diatomaceous earth, rinsing with THF. The combined filtrates were concentrated and purified by silica gel chromatography (0-10% MeOH/DCM) to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-4-benzylpiperazine-1-carboxamide (0.355 g, 64%) as a brittle pink foam. 1H NMR (400 MHz, DMSO-d6): δ 9.13 (s, 1H), 8.05 (d, J=5.7 Hz, 1H), 7.75 (d, J=2.9 Hz, 1H), 7.30-7.29 (m, 5H), 7.24-7.23 (m, 2H), 6.52 (dd, J=5.7, 2.4 Hz, 1H), 6.49 (d, J=8.9 Hz, 1H), 5.99 (s, 2H), 3.46 (s, 2H), 3.40 (t, J=4.7 Hz, 4H), 2.31 (t, J=4.7 Hz, 4H); MS (ESI) m/z: 405.2 (M+H+).

Provenance & Evidence