Hydrochloric Acid → 7,8-bis(4-chlorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione

HRID 1160222Notes

Reaction equation

HRID 1160222 reaction equation
Cl[C:2]1[C:3]([C:27]2[CH:32]=[CH:31][C:30](Cl)=[CH:29][CH:28]=2)=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:5]2[N:6]([C:8](=[O:19])[N:9]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:10]=2)[N:7]=1.C[Si]([O:38][Si](C)(C)C)(C)C.[K].[ClH:44]>C1COCC1>[Cl:44][C:30]1[CH:29]=[CH:28][C:27]([C:3]2[C:2](=[O:38])[NH:7][N:6]3[C:8](=[O:19])[N:9]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[N:10]=[C:5]3[C:4]=2[C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 595155576-chloro-7,8-bis(4-chlorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneHCID 86599933Potassium trimethylsilyloxide

Product 1

HCID 595155117,8-bis(4-chlorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dioneYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 6-chloro-7,8-bis(4-chlorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (0.48 g, 0.92 mmol) in THF (20 ml) was added potassium trimethylsilyloxide (TMSOK) (0.25 g, 1.95 mmol). The solution was heated to reflux. After 0.5 h, the solution was cooled to RT and 1N HCl solution was added until the reaction was acidic. The resulting solution was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using an automated system to give the title compound, 7,8-bis(4-chlorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione, (260 mg, 56%) as a yellow solid.

Workup

  1. temperatureThe solution was heated to reflux
  2. extractionThe resulting solution was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9b3047d238f41f69cb530eecb262a6b
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

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