Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-5-methyl-6-phenylpyridine-2-carboxamide 1-oxide

To a solution of N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (98.8 mg, 0.303 mmol) and 5-methyl-6-phenylpyridine-2-carboxylic acid 1-oxide (83.1 mg, 0.363 mmol) in N,N-dimethylformamide (1.0 mL) were added HATU (150 mg, 0.394 mmol) and N,N-diisopropylethylamine (104 μL, 0.606 mmol), and the mixture was stirred at room temperature for 3.5 hr. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The combined 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 (NH silica gel, ethyl acetate) to give a white solid. The obtained solid was washed with ethyl acetate to give the title compound (100 mg, 61%) as a white solid.

1. extractionthe mixture was extracted 3 times with ethyl acetate
2. washThe combined 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 (NH silica gel, ethyl acetate)
7. customto give a white solid
8. washThe obtained solid was washed with ethyl acetate

ORD record

ord-e0ae7a44461d41a9ab9c8930a1fe317f

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445509B2