N,N'-Dimethylethylenediamine → 2-(4-Chloro-phenyl)-6-[4-(1-methyl-pyrrolidine-3-carbonyl)-phenyl]-6h-thieno[2,3-c]pyridin-7-one, hydrochloride

HRID 2384943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384943
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:17][C:11]3[C:12](=[O:16])[NH:13][CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28]2)=[O:26])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CNCCNC.Cl.CCOCC>C(Cl)Cl.[Cu]I.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:17][C:11]3[C:12](=[O:16])[N:13]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([CH:27]5[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28]5)=[O:26])=[CH:21][CH:20]=4)[CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

9

Edukt 5

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 10953452Ether hydrochlorideHCID 576495192-(4-Chlorophenyl)-6H,7H-thieno[2,3-c]pyridin-7-oneHCID 68951075HCID 68951075, Verbindung

Produkt 1

HCID 248037462-(4-Chloro-phenyl)-6-[4-(1-methyl-pyrrolidine-3-carbonyl)-phenyl]-6h-thieno[2,3-c]pyridin-7-one, hydrochlorideAusbeute 151,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Combine 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (0.15 g, 0.57 mmol), (4-bromo-phenyl)-(1-methyl-pyrrolidin-3-yl)-methanone (0.16 g, 0.60 mmol), Cs2CO3 (0.37 g, 1.15 mmol), 1,4-dioxane (6 mL), and CuI (0.044 g, 0.23 mmol). Purge the mixture with nitrogen for 10 min. Add sym-dimethylethylene diamine (0.040 g, 0.46 mmol). Heat the mixture at 100° C. overnight. Cool the mixture to RT, dilute with CH2Cl2 (200 mL), and wash with a solution of 5% NH4OH/H2O (2×30 mL). Dry the organic layer over Na2SO4, filter, and concentrate. Filter the crude with H2O (200 mL) and Et2O (100 mL). Prepare the HCl salt by dissolving the solid in CH2Cl2 and adding 1 eq 1M HCl/ether. Allow the solution to stir for 15 min and concentrate to give 0.21 g (77%) of the title compound. LC-MS/ES m/z (35Cl) 449.0 [M+H]+.

Aufarbeitung

  1. customPurge the mixture with nitrogen for 10 min
  2. temperatureCool the mixture to RT
  3. washwash with a solution of 5% NH4OH/H2O (2×30 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. filtrationFilter the crude with H2O (200 mL) and Et2O (100 mL)
  8. customPrepare the HCl salt
  9. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-3ec9ae2f2d854c2fb27b702b4996fa66
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263772B2

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