Triethylamine → Methyl [(5-chloropyridin-2-yl)amino](oxo)acetate

2-Amino-5-chloropyridine (1.16 g) and triethylamine (1.51 ml) were dissolved in methylene chloride (26 ml), ethyl chlorooxoacetate (1.10 ml) was added to the solution under ice cooling, and the mixture was stirred at room temperature for 14 hours. After a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture to conduct liquid separation, the resultant organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1). The thus-obtained pale yellow solids were dissolved in methanol (20 ml), and the solution was stirred at 50° C. for 11 hours. The reaction mixture was concentrated under reduced pressure, and crystals deposited were collected by filtration and dried to obtain the title compound (0.43 g).

1. customliquid separation
2. dry with materialthe resultant organic layer was dried over anhydrous sodium sulfate
3. distillationthe solvent was distilled off under reduced pressure
4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)
5. dissolutionThe thus-obtained pale yellow solids were dissolved in methanol (20 ml)
6. stirringthe solution was stirred at 50° C. for 11 hours
7. concentrationThe reaction mixture was concentrated under reduced pressure, and crystals
8. filtrationdeposited were collected by filtration
9. customdried

ORD record

ord-cc0d3fd1f51542eda69fbb0e6b8d6ace

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07342014B2