Succinic anhydride → 4-[[8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methoxy]-4-oxobutanoic Acid

HRID 1166162Notes

Reaction equation

HRID 1166162 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:17])=[C:13]([CH2:15][OH:16])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[H-].[Na+].[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>C(#N)C>[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:17])=[C:13]([CH2:15][O:16][C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 24758Sodium hydrideHCID 98826348-(2,6-Dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 229974604-[[8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methoxy]-4-oxobutanoic AcidYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 8-(2,6-dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (0.2 g, 0.68 mmol) in acetonitrile (10 ml) was added sodium hydride (50% in oil) (0.036 g, 0.75 mmol) and the mixture was stirred for 5 min. To the mixture was added succinic anhydride (0.1 g, 1.0 mmol) and the reaction mixture was refluxed for 20 h. The solvent was evaporated under reduced pressure. To the residue was added water and the solid that formed was isolated by filtration and washed with acetonitrile to give 0.24 g (89%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. additionTo the residue was added water
  4. customthe solid that formed
  5. customwas isolated by filtration
  6. washwashed with acetonitrile

Sources & evidence

ORD record
ord-20e3e3f2471b4f8c8c20b605cdf5e328
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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