Pyridine → HCID 86649594, compound

To a mixture of 6-chloro-2-methylimidazo[1,2-b]pyridazine-3-carboxamide (1.5 g, 7.0 mmol) produced in the above, pyridine (1.7 mL, 21 mmol) and tetrahydrofuran (20 mL) was added dropwise under ice-cooling a solution of trifluoroacetic anhydride (1.5 mL, 11 mmol) in tetrahydrofuran (5 mL), and the mixture was stirred at room temperature for 2 hr. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0), and the obtained solution was concentrated under reduced pressure. The obtained residue was washed with diisopropyl ether to give the title compound (887 mg, 66%) as a colorless solid.

1. additionwas added dropwise under ice-
2. extractionthe mixture was extracted with ethyl acetate
3. washThe collected organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationthe insoluble material was filtered off
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)
8. concentrationthe obtained solution was concentrated under reduced pressure
9. washThe obtained residue was washed with diisopropyl ether

ORD record

ord-62d4e24343824103a546ed157fa49af7

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090601B2