Potassium Carbonate → HCID 178519726, compound

Participants

Reaction Steps

In a 25 ml flask, 6-hydroxy-nicotinic acid (102 mg, 0.73 mmol) was dissolved in N,N-dimethyl acetamide (2.7 ml) and then cooled to −15□. Thionyl chloride (0.06 ml) was added thereto and the temperature was slowly raised up to −5□ and then stirred at −5□ for 30 minutes. The mixture was cooled again to −15□ and then 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (100 mg, 0.73 mmol) and potassium carbonate (127 mg, 0.82 mmol) were added thereto and stirred for 10 minutes. The temperature was raised up to room temperature and then stirred for 14 hours. Ethyl acetate was added to the reaction mixture, and the mixture was neutralized with saturated solution of sodium hydrogen carbonate and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane:methanol=50:1. The fractions containing the product were collected and evaporated to obtain the target compound 32 as white solid (86 mg, 45%).

Provenance & Evidence