6-Chloro-8-(4-chlorophenyl)-7-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one → 8-(4-chlorophenyl)-7-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione

HRID 1160230Notes

Reaction equation

HRID 1160230 reaction equation
Cl[C:2]1[C:3]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[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:18][C:15]1[CH:16]=[CH:17][C:12]([C:4]2[C:5]3[N:6]([C:8](=[O:11])[NH:9][N:10]=3)[NH:7][C:2](=[O:29])[C:3]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 595155086-Chloro-8-(4-chlorophenyl)-7-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneHCID 86599933Potassium trimethylsilyloxideHCID 178504318HCID 178504318, compound

Product 1

HCID 595155148-(4-chlorophenyl)-7-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dioneYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 6-Chloro-8-(4-chlorophenyl)-7-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (29 mg, 0.081 mmol), prepared as described in Example 9, in THF (3 ml) was added potassium trimethylsilyloxide, TMSOK, (36 mg, 0.28 mmol). The solution was heated to refluxed for 15 min. After this time, the solution was cooled to RT. The reaction mixture was concentrated under reduced pressure. The crude material was purified by reverse phase HPLC to give the title compound, 8-(4-chlorophenyl)-7-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione, (12 mg, 32%) as a yellow solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto refluxed for 15 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0c0d73c5b2584cda9c11166d9070d601
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

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