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

HRID 1160224Notes

Reaction equation

HRID 1160224 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:42]=[CH:41][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:10]3=[N:29][N:30](COCC[Si](C)(C)C)[C:31](=[O:32])[N:9]23)=[CH:5][CH:4]=1>Cl.O1CCOCC1>[F:44][C:2]([F:1])([F:43])[C:3]1[CH:42]=[CH:41][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:10]3=[N:29][NH:30][C:31](=[O:32])[N:9]23)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 595155525-(4-(trifluoromethyl)benzyl)-7,8-bis(4-chlorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione

Product 1

HCID 595155195-(4-(Trifluoromethyl)benzyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The solution of 5-(4-(trifluoromethyl)benzyl)-7,8-bis(4-chlorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione (118 mg, 0.18 mmol) in 4M HCl in dioxane (4 ml) in a sealed tube was heated at 90° C. for 6 hours. After this time, the reaction mixture was cooled to RT, and subsequently concentrated under reduced pressure. The resulting crude product was purified by reverse phase HPLC to give the title compound, the final product, 5-(4-(trifluoromethyl)benzyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione, as colorless foam (60 mg, 66%). MS M+H=531; 1H (CDCl3) d 11.46(1H), 7.70(2H), 7.55(2H), 7.27(4H), 7.14(2H), 7.06(2H), 5.96(2H).

Workup

  1. concentrationsubsequently concentrated under reduced pressure
  2. customThe resulting crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e2f35f975ac7445b8ab2f3be82a5ba28
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

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