HCID 23155510, compound → HCID 23079300, compound

HRID 348717Notes

Reaction equation

HRID 348717 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:7]=2[CH:32]=1.C1(=O)[NH:37]C(=O)C2=CC=CC=C12.[K]>CN(C=O)C>[NH2:37][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[NH:8][C:7]=2[CH:32]=1

Participants

4

Reactant 2

HCID 23155510HCID 23155510, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 23079300HCID 23079300, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (113 mg) obtained in Example 114-3 was dissolved in DMF (2 ml) and added with potassium phthalimide (69.0 mg), followed by stirring at room temperature for 2 days. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in chloroform, followed by washing with water. After extraction with chloroform, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was dried under vacuum, and the dried product was dissolved in a 40% methylamine/methanol solution (1.5 ml), followed by stirring overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in chloroform, followed by washing with water and a 1 mol/l sodium hydroxide aqueous solution. After extraction with chloroform, the extract was washed with saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (39.8 mg) as a brown solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was then dissolved in chloroform
  4. washby washing with water
  5. extractionAfter extraction with chloroform
  6. washthe organic layer was washed with saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was dried under vacuum
  11. dissolutionthe dried product was dissolved in a 40% methylamine/methanol solution (1.5 ml)
  12. stirringby stirring overnight at room temperature
  13. customAfter completion of the reaction
  14. distillationthe solvent was distilled off under reduced pressure
  15. dissolutionthe residue was then dissolved in chloroform
  16. washby washing with water
  17. extractionAfter extraction with chloroform
  18. washthe extract was washed with saturated saline solution
  19. dry with materialdried with anhydrous sodium sulfate
  20. filtrationAfter filtration
  21. distillationthe solvent was distilled off under reduced pressure
  22. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-90dd693c4d5f4940b009f5b2995b83bd
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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