Methanol → 6-[(4-Methoxybenzyl)oxy]imidazo[1,2-a]pyridin-2-amine

HRID 2095834Notes

Reaction equation

HRID 2095834 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12](=[N:19]S(C3C=CC(C)=CC=3)(=O)=O)[N:13]([CH2:15][C:16]([NH2:18])=O)[CH:14]=2)=[CH:5][CH:4]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CO.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH2:18])[N:19]=3)[CH:14]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 669689682-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide

Product 1

HCID 581585136-[(4-Methoxybenzyl)oxy]imidazo[1,2-a]pyridin-2-amineYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide (20.8 g, 47.1 mmol) in tetrahydrofuran (200 mL) was added trifluoroacetic acid anhydride (49.5 g, 235.5 mmol) at 0° C., and the mixture was stirred for 1 hr. Methanol (100 mL) was added to the reaction mixture, 8N aqueous sodium hydroxide solution was added until pH reached 12 to 13, and the mixture was stirred at room temperature for 3 hr. Water and ethyl acetate were 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 and collected by filtration to give the title compound (8.6 g, 68%) as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-58b6ae71fe9f42d0aa52ffea5e00d6df
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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