Formaldehyde → HCID 67234441, compound

Participants

Reaction Steps

To a suspension of 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-((4-fluoropiperidin-4-yl)methoxy)quinoline dihydrochloride (0.050 g, 0.111 mmol) and triethylamine (0.0619 mL, 0.444 mmol) in 0.6 mL DCE and 0.3 mL DMF was added 37% formaldehyde in water (0.0413 mL, 0.555 mmol). After stirring at ambient temperature for 15 minutes, Na(OAc)3BH (0.0471 g, 0.222 mmol) was added, and the reaction mixture was stirred at ambient temperature for 18 hours. Another 10 equivalents of 37% formaldehyde was added, followed by 10 equivalents of Na(OAc)3BH. The reaction mixture was stirred another 6 hours, and saturated NaHCO3 was added. The mixture was extracted with dichloromethane, and the combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was purified by preparative TLC (1 mm plate, 6:1 dichloromethane: 6% NH4OH in methanol). The resulting residue was dissolved in minimal dichloromethane, and this solution was added to a vigorously stirring solution of 1.5 mL 2M HCl/ether in 15 mL ether, causing precipitation. The solids were isolated by filtration through a medium glass fritted funnel by pushing the solvent through the frit with nitrogen pressure, rinsed with ether, dried under nitrogen pressure, and dried in vacuo to give the title compound (0.015 g, 0.0323 mmol, 29.1% yield) as a white powder. MS APCI (+) m/z 392 (M+1) detected.

Provenance & Evidence