2-Pyrazinecarboxylic acid → N-Methoxy-N-methylpyrazine-2-carboxamide

To a 500 ml round bottom flask, pyrazine-2-carboxylic acid (58 g, 467.37 mmol) was suspended in dry CH2Cl2 (250 ml): oxalyl chloride (50.1 ml, 560.85 mmol) was added along with a few drops of DMF, and the mixture was stirred at room temperature for 12 hours. N,O-Dimethylhydroxylamine hydrochloride (54.7 g, 560.85 mmol) was added, and the resultant mixture was cooled down to 5° C. Triethylamine (195 ml, 1402.12 mmol) was added via a dropping funnel, and the reaction mixture was stirred at room temperature for 30 minutes before being filtered. The filter cake was washed with EtOAc, and the combined filtrate was washed with saturated sodium bicarbonate and brine, concentrated to an oil and dried under high vacuum to give the desired product (72 g).

1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
2. filtrationbefore being filtered
3. washThe filter cake was washed with EtOAc
4. washthe combined filtrate was washed with saturated sodium bicarbonate and brine
5. concentrationconcentrated to an oil
6. customdried under high vacuum

ORD-Eintrag

ord-19cf48c975be4d648d88c4f1b6fb9bcc

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08658641B2