Sodium hydride → HCID 9904880, compound

HRID 2395958Notes

Reaction equation

HRID 2395958 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:15]([CH3:24])=[C:16]([CH3:23])[C:17]2[N:18]([CH:20]=[CH:21][N:22]=2)[N:19]=1>CN(C)C=O>[CH3:24][C:15]1[C:14]([O:3][CH2:4][C:5]([CH3:12])([CH3:11])[CH2:6][S:7](=[O:9])(=[O:8])[NH2:10])=[N:19][N:18]2[CH:20]=[CH:21][N:22]=[C:17]2[C:16]=1[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 103296873-Hydroxy-2,2-dimethylpropane-1-sulfonamideHCID 15271015HCID 15271015, compound

Product 1

HCID 9904880HCID 9904880, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.59 g of 60% oily sodium hydride was suspended in 21 ml of dimethylformamide. To this suspension, 1.18 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 1 hour. To this mixture was added 1.28 g of 6-chloro-7,8-dimethylimidazo[1,2-b]pyridazine, followed by stirring at 60° C. for 40 minutes. After dimethylformamide was distilled off under reduced pressure, ice water was added to the residue, which was subsequently adjusted to pH 6 by the addition of 5 N hydrochloric acid andthen extracted with ethyl acetate-tetrahydrofuran (2:1). 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 (10:10:1). The fraction containing the desired product was concentrated and recrystallized from ethanol to yield 0.866 g of the title compound.

Workup

  1. stirringby stirring at 60° C. for 40 minutes
  2. distillationAfter dimethylformamide was distilled off under reduced pressure, ice water
  3. additionwas added to the residue, which
  4. additionwas subsequently adjusted to pH 6 by the addition of 5 N hydrochloric acid
  5. extractionandthen extracted with ethyl acetate-tetrahydrofuran (2:1)
  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 (10:10:1)
  10. additionThe fraction containing the desired product
  11. concentrationwas concentrated
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ab34d232b0b94a96a395b979e82beb94
Source dataset
uspto-grants-1996_02
Patent number
US05491145

Reaction notes

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