1,2-Diaminocyclohexane, trans- → 1-(4-Methyl-pyridin-3-yl)-3-quinoxalin-6-yl-imidazolidin-2-one

HRID 2383785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383785
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[N:18]2.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][N:10]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[N:18]3)[C:9]1=[O:13]

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 6109396-BromoquinoxalineHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 596361891-(4-Methyl-pyridin-3-yl)-3-quinoxalin-6-yl-imidazolidin-2-oneAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.84650 mmol) was reacted with 6-bromo-quinoxaline (176.9 mg, 0.84650 mmol), 1,4-dioxane (20 mL), copper iodide (16 mg, 0.084650 mmol), trans-1,2-diamino cyclohexane (29 mg, 0.2539 mmol) and potassium phosphate (538 mg, 2.539 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 175 mg of the product (67.8% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-3557df810d7b4305a66aa522cbc0a460
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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