Hydrochloric Acid → 1-Butanesulfonamide, 2-ethyl-2-(((7-methyl(1,2,4)triazolo(1,5-b)pyridazin-6-yl)oxy)methyl)-

HRID 274269

Reaction equation

HRID 274269 reaction equation
CN(C=[N:5][S:6]([CH2:9][C:10]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:11][OH:12])(=[O:8])=[O:7])C.[H-].[Na+].Cl[C:20]1[C:21]([CH3:29])=[CH:22][C:23]2[N:24]([N:26]=[CH:27][N:28]=2)[N:25]=1.Cl>O1CCCC1>[CH2:15]([C:10]([CH2:13][CH3:14])([CH2:9][S:6](=[O:7])(=[O:8])[NH2:5])[CH2:11][O:12][C:20]1[C:21]([CH3:29])=[CH:22][C:23]2[N:24]([N:26]=[CH:27][N:28]=2)[N:25]=1)[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 118051586-Chloro-7-methyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 536426363-(N,N-dimethylaminomethylene)aminosulfonyl-2,2-diethyl-1-propanol

Product 1

HCID 30737861-Butanesulfonamide, 2-ethyl-2-(((7-methyl(1,2,4)triazolo(1,5-b)pyridazin-6-yl)oxy)methyl)-Yield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.38 g of 3-(N,N-dimethylamino-methylene)aminosulfonyl-2,2-diethyl-1-propanol in 30 ml of tetrahydrofuran was added 0.23 g of 60% sodium hydride in oil and the mixture was stirred at room temperature for 1 hour. To this reaction mixture was added 0.74 g of 6-chloro-7-methyl[1,2,4]triazolo[1,5-b]pyridazine and the mixture was refluxed with stirring for 1 hour. After cooling, the reaction mixture was adjusted to pH 6 with 1N-hydrochloric acid and extracted with ethyl acetate-tetrahydrofuran (1:1). The extract was washed with water and dried and the solvent was distilled off. To the residue was added 14 ml of 6N-hydrochloric acid and the mixture was stirred at 110° C. for 30 minutes. After cooling, 100 ml of water was added to the reaction mixture and the resulting crystals were recovered by filtration and recrystallized from methanol to provide 1.16 g of the title compound. m.p. 208°-209° C.

Workup

  1. temperaturethe mixture was refluxed
  2. stirringwith stirring for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate-tetrahydrofuran (1:1)
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. additionTo the residue was added 14 ml of 6N-hydrochloric acid
  9. stirringthe mixture was stirred at 110° C. for 30 minutes
  10. temperatureAfter cooling
  11. addition100 ml of water was added to the reaction mixture
  12. filtrationthe resulting crystals were recovered by filtration
  13. customrecrystallized from methanol

Sources & evidence

ORD record
ord-fcf291590c6245a5bef8512c7a58119f
Source dataset
uspto-grants-1995_02
Patent number
US05389633

Linked notes

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