Water → 6-[(4-Methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12](=[N:20]S(C3C=CC(C)=CC=3)(=O)=O)[N:13]([CH:15]([CH3:19])[C:16]([NH2:18])=O)[CH:14]=2)=[CH:5][CH:4]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+].O>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:19])=[C:16]([NH2:18])[N:20]=3)[CH:14]=2)=[CH:5][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 2-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]propanamide (2.6 g, 5.71 mmol) in tetrahydrofuran (25 mL) was added trifluoroacetic acid anhydride (2.35 mL, 17.1 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. 8N Aqueous sodium hydroxide solution was added to the reaction mixture until it reached pH 12 to 13, and the mixture was stirred at 50° C. for 5 hr. Water and ethyl acetate 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. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (1.0 g, 68%) as a white solid.
Workup
- stirringthe mixture was stirred at 50° C. for 5 hr
- extractionthe mixture was extracted 3 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-9db161f3373b4f0595b9266791ed0a7e
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445509B2
Reaction notes
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