Triethyloxonium tetrafluoroborate → HCID 66599074, Verbindung

HRID 1889089

Reaktionsgleichung

Reaktionsgleichung von HRID 1889089
F[B-](F)(F)F.C([O+](CC)CC)C.[Cl:13][C:14]1[C:19]([Cl:20])=[C:18]([F:21])[CH:17]=[CH:16][C:15]=1[C:22]([N:24]1[CH2:29][CH2:28][NH:27][C:26](=O)[CH2:25]1)=[O:23].[CH3:31][C:32]1[O:36][C:35]([C:37]([NH:39][NH2:40])=O)=[CH:34][CH:33]=1>ClCCl>[Cl:13][C:14]1[C:19]([Cl:20])=[C:18]([F:21])[CH:17]=[CH:16][C:15]=1[C:22]([N:24]1[CH2:29][CH2:28][N:27]2[C:37]([C:35]3[O:36][C:32]([CH3:31])=[CH:33][CH:34]=3)=[N:39][N:40]=[C:26]2[CH2:25]1)=[O:23]

Komponenten

5

Edukt 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 41592505-Methyl-2-furohydrazideHCID 66599335HCID 66599335, Verbindung

Produkt 1

HCID 66599074HCID 66599074, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethyloxonium tetrafluoroborate (197 mg, 1.039 mmol) was added to a solution of the 4-[(2,3-dichloro-4-fluorophenyl)carbonyl]-2-piperazinone (I34) (275 mg, 0.945 mmol) in Dichloromethane (DCM) (6 mL) and the reaction was stirred for 1 h. To this was added the 5-methyl-2-furancarbohydrazide (I85) (159 mg, 1.134 mmol) and the reaction was stirred for 2 h. The solvent was evaporated and 1-butanol (6.00 mL) was added. The mixture was heated at reflux for 3 h. LCMS: Product peak observed. After cooling the solvent was evaporated and the residue was partitioned between water/EtOAc. The organic layer was dried (Na2SO4) and the solvent evaporated to afford a brown oil. This was purified by MDAP to afford a colourless solid of desired material in 38 mg.

Aufarbeitung

  1. stirringthe reaction was stirred for 2 h
  2. customThe solvent was evaporated
  3. addition1-butanol (6.00 mL) was added
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 3 h
  6. temperatureAfter cooling the solvent
  7. customwas evaporated
  8. customthe residue was partitioned between water/EtOAc
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. customthe solvent evaporated
  11. customto afford a brown oil
  12. customThis was purified by MDAP
  13. customto afford a colourless solid of desired material in 38 mg

Quellen und Nachweise

ORD-Eintrag
ord-933b32bdb9e4402083144a41a3e74732
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501946B2

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