Acetonitrile → HCID 68014700, compound

An acetonitrile suspension (7.5 mL) of 3-acetyl-5-methoxy-1-(pyridin-3-yl)pyridazin-4(1H)-one (0.5 g) was stirred at 70° C. for 10 min, and allowed to be cooled to room temperature. Then, N,N-dimethylformamide dimethyl acetal (2.5 mL) was added thereto, and the mixture was stirred at 80° C. for 2 hr. The insoluble material was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in ethanol (5.4 mL). To the reaction mixture was added dropwise a 10%-TFA containing ethanol solution (5.4 mL) of methylhydrazine (139 mg) under ice-cooling with stirring, and the mixture was stirred at the same temperature for 10 min, allowed to be warmed to room temperature, and stirred for 16 hr. The reaction mixture was concentrated to dryness under reduced pressure, and the residue was purified by column chromatography (NH, ethyl acetate/methanol). The eluted product was crystallized from ethyl acetate to give the title compound (47 mg) as pale-yellow crystals.

1. customThe insoluble material was removed by filtration
2. concentrationthe filtrate was concentrated to dryness under reduced pressure
3. dissolutionThe residue was dissolved in ethanol (5.4 mL)
4. additionTo the reaction mixture was added dropwise a 10%-TFA
5. additioncontaining ethanol solution (5.4 mL) of methylhydrazine (139 mg) under ice-
6. temperaturecooling
7. stirringwith stirring
8. stirringthe mixture was stirred at the same temperature for 10 min
9. temperatureto be warmed to room temperature
10. stirringstirred for 16 hr
11. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
12. customthe residue was purified by column chromatography (NH, ethyl acetate/methanol)
13. customThe eluted product was crystallized from ethyl acetate

ORD record

ord-0f138446444e4b40a7feebf7ec3971d5

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090586B2