HCID 59515506, compound → 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione

HRID 1160229Notes

Reaction equation

HRID 1160229 reaction equation
Cl[C:2]1[C:3]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.C[Si]([O:29][Si](C)(C)C)(C)C.[K].[Si](O[K])(C)(C)C>C1COCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:3]2[C:2](=[O:29])[NH:7][N:6]3[C:8](=[O:11])[NH:9][N:10]=[C:5]3[C:4]=2[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 59515506HCID 59515506, compoundHCID 86599933Potassium trimethylsilyloxideHCID 178504318HCID 178504318, compound

Product 1

HCID 595155337-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dioneYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 6-chloro-7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (28 mg, 0.078 mmol), prepared as described in Example 8B, in THF (3 ml) was added potassium trimethylsilyloxide, TMSOK, (36 mg, 0.28 mmol). The reaction mixture was refluxed for 1 hour. After this time, the solution was cooled to RT. The solution was concentrated under reduced pressure. The resulting crude product was purified by reverse phase HPLC to give the title compound, 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione, (8 mg, 22%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. concentrationThe solution was concentrated under reduced pressure
  3. customThe resulting crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5a4860bd1eb249498ee4be46114b0b12
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

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