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 1160222ノート

反応式

HRID 1160222 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b9b3047d238f41f69cb530eecb262a6b
出典データセット
uspto-grants-2010_10
特許番号
US07816357B2

反応ノート

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