Dimethylformamide → HCID 22388033, compound

HRID 1699946Notes

Reaction equation

HRID 1699946 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]=3[Cl:22])[C:9]([CH3:11])=[N:10][C:5]2=[CH:4][CH:3]=1.[C:23](Cl)(=O)[C:24](Cl)=O.CN(C)C=O>ClCCl>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([O:21][CH:24]4[CH2:23][CH2:5][CH2:4][CH2:3][CH2:2]4)=[O:20])=[CH:15][C:14]=3[Cl:22])[C:9]([CH3:11])=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 22388035HCID 22388035, compound

Product 1

HCID 22388033HCID 22388033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-3-(2-chloro-4-carboxybenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (525 mg) in dichloromethane (5 ml) were added oxalyl chloride (0.36 ml) and N,N-dimethylformamide (0.03 ml), and the mixture was stirred at room temperature for 1 hr and concentrated under reduced pressure. Dichloromethane (5 ml) was added and dissolved, and trimethylamine (698 mg), 4-dimethylaminopyridine (10 mg) and cyclohexanol (1.38 g) were successively added under ice-cooling. The mixture was stirred under ice-cooling for 30 min and at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added for partitioning. The organic layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hexane (20 ml) was added to the residue and the mixture was heated. The black insoluble matter was removed by filtration and the filtrate was allowed to cool. The precipitated crystals were collected by filtration, dried under reduced pressure and by heating to give the objective compound (533 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionDichloromethane (5 ml) was added
  3. dissolutiondissolved
  4. additiontrimethylamine (698 mg), 4-dimethylaminopyridine (10 mg) and cyclohexanol (1.38 g) were successively added under ice-
  5. temperaturecooling
  6. stirringThe mixture was stirred under ice-
  7. temperaturecooling for 30 min and at room temperature for 30 min
  8. concentrationThe reaction mixture was concentrated under reduced pressure, and water and ethyl acetate
  9. additionwere added
  10. customfor partitioning
  11. washThe organic layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. additionHexane (20 ml) was added to the residue
  15. temperaturethe mixture was heated
  16. customThe black insoluble matter was removed by filtration
  17. temperatureto cool
  18. filtrationThe precipitated crystals were collected by filtration
  19. customdried under reduced pressure
  20. temperatureby heating

Sources & evidence

ORD record
ord-109e8f863b8d42e5a4f9de6f5c955a64
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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