Pyridine → HCID 136005966, compound

HRID 915969Notes

Reaction equation

HRID 915969 reaction equation
N1C=CC=CC=1.CS(O)(=O)=O.[CH:12]1([C:18]2[C:26]3[C:25](=[O:27])[NH:24][C:23]([C:28]4[CH:33]=[CH:32][C:31](N5CCC(O)CC5)=[CH:30][C:29]=4OC)=[N:22][C:21]=3[N:20]([CH3:43])[N:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[Br:44]C1C=CC(C(Cl)=O)=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:44][C:31]1[CH:32]=[CH:33][C:28]([C:23]2[NH:24][C:25](=[O:27])[C:26]3[C:18]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)=[N:19][N:20]([CH3:43])[C:21]=3[N:22]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 685154-Bromobenzoyl chloride2×HCID 516892Sodium BicarbonateHCID 136333294HCID 136333294, compound

Product 1

HCID 136005966HCID 136005966, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 30 ml pyridine solution of 2.2 g (10 mmol) of the compound obtained in Example 32, 2.8 g (13 mmol) of p-bromobenzoyl chloride was added, and the mixture was stirred at room temperature for 3 hours. Further, 1.0 g (4.5 mmol) of p-bromobenzoyl chloride was added, and the mixture was stirred at room temperature for 4 hours. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. To the residue, 80 ml of ethanol and 40 ml of a 1M aqueous solution of sodium hydroxide were added, and the mixture was heated under reflux for 8 hours. Then, the reaction mixture was cooled to room temperature, and acetic acid was added. Precipitated solids were collected by filtration, the solids obtained were dissolved in chloroform, and the solution was washed with sodium hydrogen carbonate, water and a saturated aqueous solution of sodium chloride in this order. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized (ethanol) to obtain 590 mg (15%) of the captioned compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. additionTo the residue, 80 ml of ethanol and 40 ml of a 1M aqueous solution of sodium hydroxide were added
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 8 hours
  9. temperatureThen, the reaction mixture was cooled to room temperature
  10. additionacetic acid was added
  11. customPrecipitated solids
  12. filtrationwere collected by filtration
  13. customthe solids obtained
  14. washthe solution was washed with sodium hydrogen carbonate, water
  15. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  16. distillationthe solvent was distilled off under reduced pressure
  17. customThe residue was recrystallized (ethanol)

Sources & evidence

ORD record
ord-f59fc4017b634d9fb4c1cf5316f9cd0a
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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