Triethyloxonium tetrafluoroborate → HCID 66599478, Verbindung

HRID 1889083

Reaktionsgleichung

Reaktionsgleichung von HRID 1889083
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=O)[CH2:13]1)=[O:11].F[B-](F)(F)F.C([O+](CC)CC)C.[F:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]([NH:40][NH2:41])=O)=[N:36][CH:37]=1>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:38]([C:35]3[CH:34]=[CH:33][C:32]([F:31])=[CH:37][N:36]=3)=[N:40][N:41]=[C:14]2[CH2:13]1)=[O:11]

Komponenten

5

Edukt 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 552809675-FluoropicolinohydrazideHCID 665993354-[(2,3-Dichloro-4-fluorophenyl)carbonyl]-2-piperazinone

Produkt 1

HCID 66599478HCID 66599478, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-[(2,3-dichloro-4-fluorophenyl)carbonyl]-2-piperazinone (I34) (5.08 g, 17.45 mmol) in Dichloromethane (DCM) (80 mL) was added triethyloxonium tetrafluoroborate (3.48 g, 18.32 mmol). The solution was then stirred under argon for 20 minutes before 5-fluoro-2-pyridinecarbohydrazide (I24) (3.25 g, 20.94 mmol) was added. The solution was then stirred for a further 3 hours, before the solvent was concentrated and n-butanol (80 mL) was added. The solution was then stirred, under reflux and argon, for 3 hours before being cooled to room temperature. The solvent was then evaporated in vacuo and the remaining residue was partioned between DCM (100 mL) and water (50 mL), before being dried over anhydrous sodium suphate. The sodium sulphate was then removed by filtration, and the solvent was evaporated in vacuo. The remaining residue was then purified by flash chromatography (Isolera 340 g cartridge) with a gradient of 0-10% MeOH in DCM, TLC confirmed product location and the solvent from the combined fractions was evaporated in vacuo. The remaining solid was then recrystallised from ethyl acetate to yield the product in 2.067 g.

Aufarbeitung

  1. additionwas added
  2. concentrationwas concentrated
  3. additionn-butanol (80 mL) was added
  4. stirringThe solution was then stirred
  5. temperatureunder reflux
  6. customThe solvent was then evaporated in vacuo
  7. dry with materialbefore being dried over anhydrous sodium suphate
  8. customThe sodium sulphate was then removed by filtration
  9. customthe solvent was evaporated in vacuo
  10. customThe remaining residue was then purified by flash chromatography (Isolera 340 g cartridge) with a gradient of 0-10% MeOH in DCM, TLC
  11. customthe solvent from the combined fractions was evaporated in vacuo
  12. customThe remaining solid was then recrystallised from ethyl acetate
  13. customto yield the product in 2.067 g

Quellen und Nachweise

ORD-Eintrag
ord-616eeb7f82e542329fcbf6f9d641d1dd
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501946B2

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