Hydrochloric Acid → 1-Propanesulfonamide, 2,2-dimethyl-3-((7,8-dimethyl(1,2,4)triazolo(1,5-b)pyridazin-6-yl)oxy)-

HRID 274267Notes

Reaction equation

HRID 274267 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]([N:20]=[CH:21][N:22]=2)[N:19]=1.Cl>CN(C)C=O.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[N:20]=[CH:21][N:22]=[C:17]2[C:16]=1[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 103296873-Hydroxy-2,2-dimethylpropane-1-sulfonamideHCID 152348786-Chloro-7,8-dimethyl[1,2,4]triazolo[1,5-b]pyridazine

Product 1

HCID 30737851-Propanesulfonamide, 2,2-dimethyl-3-((7,8-dimethyl(1,2,4)triazolo(1,5-b)pyridazin-6-yl)oxy)-Yield 14.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 30 ml of dimethylformamide was suspended 1.38 g of 60% sodium hydride in oil, followed by addition of 2.51 g of 3-hydroxy-2,2-dimethyl-1-propanesulfonamide and the mixture was stirred under reduced pressure at room temperature for 1 hour. To this was added 2.56 g of 6-chloro-7,8-dimethyl[1,2,4]triazolo[1,5-b]pyridazine and the mixture was stirred at room temperature for 3 hours. Following addition of 100 ml of iced water, the reaction mixture was adjusted to pH 6 with 5N-hydrochloric acid and extracted with 3 portions of ethyl acetate-tetrahydrofuran (2:1). The extract was washed with 20 ml of saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was subjected to silica gel column chromatography, elution being carried out with dichloromethane-methanol (30:1). The fractions containing the desired product were pooled and concentrated to provide 0.63 g of the title compound. m.p. 175°-177° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with 3 portions of ethyl acetate-tetrahydrofuran (2:1)
  3. washThe extract was washed with 20 ml of saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. washthe residue was subjected to silica gel column chromatography, elution
  7. additionThe fractions containing the desired product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3f85b4ed28f14519ab358ff0043c54f3
Source dataset
uspto-grants-1995_02
Patent number
US05389633

Reaction notes

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