Sodium hydride → HCID 16732293, compound

A solution of 6-oxo-1,6-dihydropyridazine-3-carboxylic acid (1.4 g) and 1,1′-carbonylbis(1H-imidazole) (2.1 g) in N,N-dimethylformamide (80 mL) was stirred at 60° C. for 1 hr. The mixture was cooled to room temperature, and N′-hydroxyethanimidamide (963 mg) was added. Sodium hydride (520 mg) was slowly added, and the mixture was stirred at 100° C. for 8 hr. The mixture was cooled to room temperature, diluted with saturated aqueous ammonium chloride solution (100 mL) and saturated aqueous sodium chloride solution (100 mL), and the mixture was extracted 3 times with ethyl acetate-tetrahydrofuran (1:1, v/v, 100 mL). The organic layers were combined, and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was suspended in diethyl ether and diisopropyl ether and the precipitate was collected by filtration to give the object product (1.1 g, 60%).

1. temperatureThe mixture was cooled to room temperature
2. extractionthe mixture was extracted 3 times with ethyl acetate-tetrahydrofuran (1:1, v/v, 100 mL)
3. dry with materialdried over sodium sulfate
4. customthe solvent was evaporated under reduced pressure
5. filtrationdiisopropyl ether and the precipitate was collected by filtration

ORD record

ord-69fa4b5422934b9fb65d26da61e77594

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575167B2