Trifluoroacetic acid → N-(6-hydroxy-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide

HRID 2095840Notes

Reaction equation

HRID 2095840 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:24])=[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]([C:15]([CH3:24])=[C:16]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])[N:17]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 58158603N-{6-[(4-methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

Product 1

HCID 58158508N-(6-hydroxy-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamideYield 14.1%

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

To a solution of N-{6-[(4-methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide (700 mg, 1.99 mmol) and anisole (1.73 mL, 15.9 mmol) in trifluoromethylbenzene (7 mL) was added trifluoroacetic acid (1.4 mL), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted 4 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 to give the title compound (65 mg, 14%) as a slightly-yellow solid.

Workup

  1. extractionthe mixture was extracted 4 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

Sources & evidence

ORD record
ord-bf44fecf909648f883b91bd8805a3d1d
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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