Acetic Acid → HCID 178518684, compound

Participants

Reaction Steps

To a solution of 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine dihydro-chloride (46 mg, 0.15 mmol) and 4-(8-oxo-3-phenyl-7,8-dihydro-1,7-naphthyridin-2-yl)benzaldehyde (40 mg, 0.12 mmol) in dry DMF (0.5 mL) was added triethylamine (55 μL, 0.40 mmol). After stirring for 10 minutes acetic acid (70 μL, 1.20 mmol) was added and the mixture was stirred at room temperature over night. Then sodium triacetoxy borohydride (52 mg, 0.24 mmol) was added in one portion. After two hours the reaction was complete and some methanol was added. This reaction mixture was concentrated to a smaller volume and adsorbed on silica gel and purified by column chromatography eluting with 0.5-13% methanol/ethyl acetate (sat'd NH3). The appropriate fractions were combined and the solvents removed in vacuo. The residue was triturated with diethyl ether to give pure title compound as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 14.34 (1H, br s), 11.56 (1H, d, J=5.6 Hz), 8.68 (1H, br s), 8.15 (1H, s), 8.03 (1H, m), 7.96 (1H, m), 7.50 (1H, br s), 7.22-7-38 (10H, m), 6.62 (1H, d, J=6.8 Hz), 3.49 (2H, s), 2.84 (2H, brm), 2.69 (1H, m), 2.07 (2H, brt, J=11 Hz), 1.94 (2H, m), 1.78 (2H, m). m/e (m+1): 540.3, 270.8 [(m+2)/2].

Provenance & Evidence