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Water → 6-[(4-Methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-amine

HRID 2095838
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Reaction equation

HRID 2095838 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 669690882-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]propanamide

Product 1

HCID 581585166-[(4-Methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-amineYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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

  1. stirringthe mixture was stirred at 50° C. for 5 hr
  2. extractionthe mixture was extracted 3 times with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washThe obtained residue was washed with ethyl acetate
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9db161f3373b4f0595b9266791ed0a7e
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08445509B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes