Cesium carbonate → N-{1-[4-(Isoquinolin-3-ylamino)-benzenesulfonyl]-piperidin-4-yl}-acrylamide

HRID 337237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337237
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[N:51]=1.[NH2:60][C:61]1[CH:66]=[CH:65][C:64]([S:67]([N:70]2[CH2:75][CH2:74][CH:73]([NH:76][C:77](=[O:80])[CH:78]=[CH2:79])[CH2:72][CH2:71]2)(=[O:69])=[O:68])=[CH:63][CH:62]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:52]1[C:57]2[C:58](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:59]=[C:50]([NH:60][C:61]2[CH:62]=[CH:63][C:64]([S:67]([N:70]3[CH2:71][CH2:72][CH:73]([NH:76][C:77](=[O:80])[CH:78]=[CH2:79])[CH2:74][CH2:75]3)(=[O:68])=[O:69])=[CH:65][CH:66]=2)[N:51]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 71618273N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide

Produkt 1

HCID 86674091N-{1-[4-(Isoquinolin-3-ylamino)-benzenesulfonyl]-piperidin-4-yl}-acrylamideAusbeute 0,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Tris(dibenzylideneacetone)dipalladium (0) (0.05 g, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.015 g, 0.03 mmol), cesium carbonate (0.5 g, 2.0 mmol) and 2-chloroquinoline (0.085 g, 0.52 mmol) were added sequentially to a stirred solution of N-[1-(4-amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide in dry dioxane (5 ml) under a nitrogen atmosphere. The mixture was heated to 110° C. for 12 hours. After this time the mixture was cooled to room temperature, filtered through a pad of celite, the celite was washed with EtOAc (50 ml) and the filtrate was washed sequentially with citric acid (10% solution, 20 ml) and brine (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by prep HPLC to give the title compound (0.002 g, 0.5% yield) as a white solid.

Aufarbeitung

  1. temperatureAfter this time the mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washthe celite was washed with EtOAc (50 ml)
  4. washthe filtrate was washed sequentially with citric acid (10% solution, 20 ml) and brine (20 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5a056d78a55a45b3951f9735550cfac0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889716B2

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