2-Fluorobenzenesulphonyl chloride → 2-(2-Fluoro-benzenesulfonyl)-octahydro-pyrido[1,2-a]pyrazin-6-one

HRID 2194362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194362
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][CH:2]12.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.CC#N>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([N:6]1[CH2:5][CH2:4][N:3]2[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][CH:2]2[CH2:1]1)(=[O:21])=[O:20]

Komponenten

5

Edukt 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 22562193Hexahydro-1H-pyrido[1,2-a]pyrazin-6(2H)-one

Produkt 1

HCID 441929292-(2-Fluoro-benzenesulfonyl)-octahydro-pyrido[1,2-a]pyrazin-6-oneAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of octahydro-pyrido[1,2-a]pyrazin-6-one (compound of Description 12, 20 mg, 0.13 mmol) in DCM (1 ml), TEA (16 mg, 0.16 mmol) and a solution of 2-fluoro-benzenesulfonyl chloride (25 mg, 0.13 mmol) in CH3CN (1 ml) were added at 0° C. After stirring 3 hours at room temperature, the solvent was evaporated. The residue was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash chromatography (from DCM to DCM/MeOH/32% NH4OH 95/5/0.5 respectively) to afford the title compound (18 mg, 44% yield).

Aufarbeitung

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (from DCM to DCM/MeOH/32% NH4OH 95/5/0.5 respectively)

Quellen und Nachweise

ORD-Eintrag
ord-139eec7709f44ef88444b5518247a3d6
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334286B2

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