Diisopropylethylamine → N-[3-chloro-4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Temperatur

60 °C

To a solution of N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.292 mmol) and 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (94 mg, 0.38 mmol) in N,N-dimethylformamide (1 mL) were added N,N-diisopropylethylamine (100 μL, 0.583 mmol) and HATU (144 mg, 0.380 mmol), and the mixture was stirred at 60° C. for 4 hr. Ethyl acetate, tetrahydrofuran and saturated aqueous sodium hydrogen carbonate solution was 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 purified by silica gel column chromatography (ethyl acetate alone) to give a white solid. The obtained solid was washed with ethyl acetate and collected by filtration to give the title compound (120.2 mg, 72%) 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. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate alone)
7. customto give a white solid
8. washThe obtained solid was washed with ethyl acetate
9. filtrationcollected by filtration

ORD-Eintrag

ord-d4ac3aaf3ffd4070a51313850ac7a809

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08445509B2