Hydrochloric Acid → HCID 68501669, compound

HRID 1929525Notes

Reaction equation

HRID 1929525 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([CH:8](C#N)[C:9]2[CH:10]=[CH:11][C:12]([F:17])=C([CH:16]=2)C#N)=[CH:4][C:3]=1[CH2:20][CH3:21].Cl.[CH3:23][C:24]([O-:26])=[O:25].[Na+].[OH-:28].[Na+]>CC(O)=O.O.CCOC(C)=O>[CH2:20]([C:3]1[C:2](=[O:28])[NH:7][N:6]=[C:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([F:17])=[C:23]([CH:16]=2)[C:24]([OH:26])=[O:25])[CH:4]=1)[CH3:21]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 86632295HCID 86632295, compound

Product 1

HCID 68501669HCID 68501669, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of A1 (1 eq) in AcOH, cone. HCl and H2O (1:2:1, 0.065 M) was heated at reflux overnight, then cooled to RT and diluted with H2O and EtOAc and separated. The aqueous phase was washed with EtOAc and the combined extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The crude was dissolved in AcOH and NaOAc (2 eq) was added. The resulting solution was heated at reflux for 1 hr. The reaction mixture was cooled and the mixture was extracted with EtOAc. The organic phase was washed twice with brine, dried (Na2SO4) and the solvent removed under reduced pressure. The residue was taken up in H2O and to the resulting suspension was added an aqueous solution of 23 M NaOH (8 eq) and heated to 90° C. for 30 min. The reaction solution was cooled then acidified to pH 4 with 2 M HCl. The mixture stirred for 10 min and filtered. The resulting solid was washed sequentially with H2O, hexanes, Et2O, EtOAc and dried under high vacuum to give the title compound as a pale orange powder.

Workup

  1. temperatureat reflux overnight
  2. customseparated
  3. washThe aqueous phase was washed with EtOAc
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe crude was dissolved in AcOH
  8. temperatureThe resulting solution was heated
  9. temperatureat reflux for 1 hr
  10. temperatureThe reaction mixture was cooled
  11. extractionthe mixture was extracted with EtOAc
  12. washThe organic phase was washed twice with brine
  13. dry with materialdried (Na2SO4)
  14. customthe solvent removed under reduced pressure
  15. temperatureheated to 90° C. for 30 min
  16. temperatureThe reaction solution was cooled
  17. filtrationfiltered
  18. washThe resulting solid was washed sequentially with H2O, hexanes, Et2O, EtOAc
  19. customdried under high vacuum

Sources & evidence

ORD record
ord-af3581b767eb4e44ae243279a6ec5ad5
Source dataset
uspto-grants-2012_05
Patent number
US08188084B2

Reaction notes

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