Glutaric anhydride → 5-[[8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methoxy]-5-oxopentanoic Acid

HRID 1166164Notes

Reaction equation

HRID 1166164 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:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26]1>O1CCCC1>[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:32])[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7940Glutaric anhydrideHCID 24758Sodium hydrideHCID 98826348-(2,6-Dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 99313345-[[8-(2,6-Dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-yl]methoxy]-5-oxopentanoic AcidYield 8.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(2,6-dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (0.3 g, 1.0 mmol) in tetrahydrofuran(10 ml) was added sodium hydride (50% in oil) (0.054 g, 1.1 mmol) and the mixture was stirred for 10 min. To the mixture was added glutaric anhydride (0.13 g, 1.1 mmol) and the reaction mixture was refluxed for 20 h. The solvent was evaporated under reduced pressure. The residue was partitioned between dichloromethane and water. The pH was adjusted to 4 with 2M HCl. The organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (94:6) as eluent gave 0.034 g (8%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-3f2959993496411a8fc690f5b4ce952b
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

Loading…