Sodium Bicarbonate → HCID 60162050, compound

Participants

Reaction Steps

To a solution of 3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propanal (150 mg, 1.13 mmol) in N,N-dimethylformamide (5 ml) was added 6-[(4R)-4-amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (synthesized using [(3R)-5-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester synthesized with reference to WO2004/22536 in the same manner as in Reference Examples 20, 21 and 22; 303 mg, 1.22 mmol) and the mixture was stirred at room temperature for 1 hour. After cooling the reaction solution on ice, sodium triacetoxyborohydride (388 mg, 1.83 mmol) was added thereto and the mixture was stirred at room temperature for 2 hours. A sodium hydrogen carbonate aqueous solution was added, the reaction solution was extracted with ethyl acetate and the extract was washed with water and saturated sodium chloride solution. The obtained organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The obtained crude product was purified by thin layer chromatography (dichloromethane/methanol) so as to yield 15 mg (3%) of the title compound.

Provenance & Evidence