Sodium Chloride → Piperazine, 1-methyl-4-((3-((1,2,4)triazolo(1,5-b)pyridazin-6-yloxy)propyl)sulfonyl)-

HRID 274284Notes

Reaction equation

HRID 274284 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([S:10]([CH2:13][CH2:14][CH2:15][OH:16])(=[O:12])=[O:11])[CH2:6][CH2:5]1.Cl[C:18]1[CH:19]=[CH:20][C:21]2[N:22]([N:24]=[CH:25][N:26]=2)[N:23]=1.[Cl-].[Na+]>CN(C)C=O.O1CCCC1>[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([S:10]([CH2:13][CH2:14][CH2:15][O:16][C:18]2[CH:19]=[CH:20][C:21]3[N:22]([N:24]=[CH:25][N:26]=3)[N:23]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazineHCID 152348893-(1-Methyl-4-piperazinylsulfonyl)-1-propanol

Product 1

HCID 3073803Piperazine, 1-methyl-4-((3-((1,2,4)triazolo(1,5-b)pyridazin-6-yloxy)propyl)sulfonyl)-Yield 60.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of dimethylformamide was suspended 0.21 g of 60% sodium hydride in oil followed by addition of 1.12 g of 3-(1-methyl-4-piperazinylsulfonyl)-1-propanol and the mixture was stirred under reduced pressure at room temperature for 75 minutes. Then, 0.773 g of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine was added and the mixture was further stirred at room temperature for 1.5 hours. Following addition of 40 ml of ice water, the reaction mixture was saturated with sodium chloride. The aqueous layer was extrated with tetrahydrofuran and the extrat was dried over 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 (10:1). The fractions containing the desired product were pooled and concentrated to provide 1.032 g of the title compound. m.p. 140°-141° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1.5 hours
  2. dry with materialthe extrat was dried over magnesium sulfate
  3. distillationThe solvent was then distilled off under reduced pressure
  4. washthe residue was subjected to silica gel column chromatography, elution
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2714be0aec064fd795bbb0c8e695f67d
Source dataset
uspto-grants-1995_02
Patent number
US05389633

Reaction notes

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