Imidazo(1,2-b)pyridazine, 6-chloro- → 6-[(3-Sulfamoyl-2,2-dimethylpropyl)thio]imidazo[1,2-b]pyridazine

HRID 465941Notes

Reaction equation

HRID 465941 reaction equation
[SH:1][CH2:2][C:3]([CH3:10])([CH3:9])[CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].C[O-].[Na+].CO.Cl[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:23]=[CH:24][N:25]=2)[N:22]=1>CO>[S:5]([CH2:4][C:3]([CH3:10])([CH3:9])[CH2:2][S:1][C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:23]=[CH:24][N:25]=2)[N:22]=1)(=[O:7])(=[O:6])[NH2:8]

Participants

5

Reactant 3

HCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 104649823-Mercapto-2,2-dimethyl-1-propylsulfonamideHCID 23694274Sodium methanolate methanol

Product 1

HCID 99720306-[(3-Sulfamoyl-2,2-dimethylpropyl)thio]imidazo[1,2-b]pyridazineYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.37 g of 3-mercapto-2,2-dimethyl-1-propylsulfonamide and 0.37 g of 28% sodium methoxide-methanol solution in 50 ml of methanol was added 0.31 g of 6-chloroimidazo[1,2-b]pyridazine, followed by refluxing at 80°-85° C. for 3 hours. The reaction solution was concentrated under reduced pressure. The residue to which 30 ml of water were added was extracted with tetrahydrofuran and ethyl acetate (1:1). The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was recrystallized from ethanol to obtain 0.4 g of the title compound.

Workup

  1. temperatureby refluxing at 80°-85° C. for 3 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionThe residue to which 30 ml of water were added
  4. extractionwas extracted with tetrahydrofuran and ethyl acetate (1:1)
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-adc395e2f36341b8a96f5d1ee8e1d9d7
Source dataset
uspto-grants-1992_10
Patent number
US05155108

Reaction notes

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