Diisopropylethylamine → N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)pyridin-2-yl]-6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide

To a solution of N-{6-[(6-aminopyridin-3-yl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide (200 mg, 0.647 mmol) and 6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid (178 mg, 0.776 mmol) in N,N-dimethylformamide (3 mL) were added N,N-diisopropylethylamine (233 μL, 1.29 mmol) and HATU (320 mg, 0.841 mmol), and the mixture was stirred at room temperature for 6 hr. Ethyl acetate, tetrahydrofuran and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration. The obtained white solid was suspended in methyl ethyl ketone (2 mL), and the mixture was stirred at 80° C. for 17 hr. The suspension was collected by filtration to give the title compound (175 mg, 52%) as a white solid.

1. extractionthe mixture was extracted 3 times with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. customthe solvent was evaporated under reduced pressure
6. washThe obtained residue was washed with ethyl acetate
7. filtrationcollected by filtration
8. stirringthe mixture was stirred at 80° C. for 17 hr
9. filtrationThe suspension was collected by filtration

ORD record

ord-146483bc3804462eb25256911c5bd31d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445509B2