Sodium Bicarbonate → HCID 57815362, compound

Participants

Reaction Steps

To 76 mg of (7-(methylamino)-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde, a solution of 0.11 g of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate in 2.5 mL of dichloromethane and 19 μL of acetic acid were added, and the mixture was stirred at room temperature for 5 minutes. To the reaction mixture, 0.10 g of sodium triacetoxyborohydride was added, and the mixture was stirred at the same temperature for 2 hours 20 minutes. Thereto was added chloroform and the reaction mixture was adjusted to pH 8.3 with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using an eluent of chloroform:methanol=19:1 to obtain 55 mg of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-(methylamino)-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a light yellow oily substance.

Provenance & Evidence