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), and ethyl chlorooxoacetate (1.10 mL) was added thereto under ice cooling, followed by stirring at room temperature for 14 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture to partition the mixture, and the organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1). The resultant pale-yellow solid was dissolved in methanol (20 mL), and the solution was stirred at 50° C. for 11 hours. The reaction mixture was concentrated under reduced pressure. The precipitated crystals were collected by filtration, and were dried, to thereby give the title compound (0.43 g).

1. customto partition the mixture
2. dry with materialthe organic layer was dried over sodium sulfate anhydrate
3. distillationThe solvent was distilled away under reduced pressure
4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)
5. dissolutionThe resultant pale-yellow solid was 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
8. filtrationThe precipitated crystals were collected by filtration
9. customwere dried

ORD record

ord-34cc499268d947ba9a6ff01894060f0d

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576135B2