1-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperidine-4-carboxamide → N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-1-methylpiperidine-4-carboxamide

Participants

Reaction Steps

A solution of 1-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperidine-4-carboxamide (0.20 g, 0.560 mmol) in 2:1 EtOAc/MeOH (15 mL) was treated with Palladium on carbon (50% wet) (0.066 g, 0.056 mmol) was hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to dryness to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-1-methylpiperidine-4-carboxamide (130 mg, 71%). 1H NMR (400 MHz, DMSO-d6): δ 10.43 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 7.77 (d, J=2.9 Hz, 1H), 7.60 (d, J=2.4 Hz, 1H), 7.26 (dd, J=8.9, 3.0 Hz, 1H), 6.63 (dd, J=5.7, 2.4 Hz, 1H), 6.51 (d, J=8.9 Hz, 1H), 6.01 (s, 2H), 2.77 (m, 2H), 2.39 (m, 1H), 2.14 (s, 3H), 1.83 (m, 2H), 1.67 (m, 2H), 1.57 (m, 2H); MS (ESI) m/z: 328.2 (M+H+).

Provenance & Evidence