Trifluoroacetic acid → N-(6-Hydroxyimidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamide
Reaction equation
COC1C=CC(C[O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:17]=3)[CH:14]=2)=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>FC(C1C=CC=CC=1)(F)F>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH:15]=[C:16]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])[N:17]=2)[CH:14]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-{6-[(4-methoxybenzyl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide (10.1 g, 29.9 mmol) and anisole (25.97 mL, 239.2 mmol) in trifluoromethylbenzene (200 mL) was added trifluoroacetic acid (40.4 mL), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted 5 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (5.7 g, 88%) as a pale-brown solid.
Workup
- extractionthe mixture was extracted 5 times with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe solvent was evaporated under reduced pressure
- washThe obtained residue was washed with ethyl acetate
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-e7b431dde53340de96cf9479a5816ad9
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445509B2
Reaction notes
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