Trimethyl orthoacetate → 3-methyl-9-phenyl-8-(4-((4-(5-(pyridin-2-yl)-1H-1,2,4-triazol-3-yl)piperidin-1-yl)methyl)phenyl)-[1,2,4]triazolo[3,4-f][1,6]naphthyridine

Participants

Reaction Conditions

Reaction Steps

To 5-hydrazino-3-phenyl-2-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)-1,6-naphthyridine (2-1) (55 mg, 0.101 mmol) in DMF (1.0 mL) was added trimethyl orthoacetate (0.63 mL, 5.04 mmol). The reaction mixture was stirred at 100° C. for 3 hours, and then concentrated in vacuo, and chromatographed to furnish the desired 3-methyl-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine (2-2) (28 mg) as its trifluoroacetic acid salt. 1H NMR: (500 MHz, CDCl3) δ 8.87 (s, 1H), 8.65 (d, J=6.4 Hz, 1H), 8.33 (d, J=7.5 Hz, 1H), 8.11 (d, J=7.8 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.49-7.41 (m, 3H), 7.36-7.30 (m, 8H), 3.61 (s, 2H), 3.02-3.00 (m, 2H), 3.00-2.84 (m, 1H), 2.25-2.21 (m, 2H), 2.10-1.83 (m, 4H), 1.97 (s, 3H).

Provenance & Evidence