Sodium hydride → HCID 10782939, compound

HRID 2395963Notes

Reaction equation

HRID 2395963 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([CH3:12])([CH3:11])[CH2:6][S:7]([NH2:10])(=[O:9])=[O:8].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2=[N:24][CH:25]=[CH:26][N:16]2[N:15]=1>CN(C)C=O>[CH3:11][C:5]([CH3:12])([CH2:6][S:7](=[O:9])(=[O:8])[NH2:10])[CH2:4][O:3][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2=[N:24][CH:25]=[CH:26][N:16]2[N:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 103296873-Hydroxy-2,2-dimethylpropane-1-sulfonamideHCID 15271019HCID 15271019, compound

Product 1

HCID 10782939HCID 10782939, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.293 g of 60% oily sodium hydride was suspended in 10 ml of dimethylformamide. To this suspension, 0.577 g of 3-hydroxy-2,2-dimethyl -1-propanesulfonamide was added, followed by stirring at room temperature (15° to 20° C.) under reduced pressure for 30 minutes. To this mixture was added 0.703 g of 6-chloroimidazo[2,1-a]phthalazine, followed by stirring at room temperature for 3 hours. After dimethylformamide was distilled off under reduced pressure, ice water was added to the residue, which was subsequently adjusted to pH 5.0 by the addition of 5 N hydrochloric acid and then extracted with ethyl acetate-tetrahydrofuran (1:1). The extract was washed with 20 ml of saturated saline and then dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with dichloromethane-ethyl acetate-methanol (20:20:1). The fraction containing the desired product was concentrated and ethyl ether was added to separate a crystal, which was collected by filtration, to yield 0.769 g of the title compound.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. distillationAfter dimethylformamide was distilled off under reduced pressure, ice water
  3. additionwas added to the residue, which
  4. additionwas subsequently adjusted to pH 5.0 by the addition of 5 N hydrochloric acid
  5. extractionextracted with ethyl acetate-tetrahydrofuran (1:1)
  6. washThe extract was washed with 20 ml of saturated saline
  7. dry with materialdried over magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. washeluted with dichloromethane-ethyl acetate-methanol (20:20:1)
  10. additionThe fraction containing the desired product
  11. concentrationwas concentrated
  12. additionethyl ether was added
  13. customto separate a crystal, which
  14. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-2b0b0a46671d43a2b1e681061374a688
Source dataset
uspto-grants-1996_02
Patent number
US05491145

Reaction notes

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