1,2-Diaminocyclohexane, trans- → 1-Benzo[b]thiophen-3-yl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383822

Reaktionsgleichung

Reaktionsgleichung von HRID 2383822
[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[C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[S:18][CH:19]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:18]1[CH:19]=[C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])[C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]1=2

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 123250Benzo(b)thiophene, 3-bromo-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 596361961-Benzo[b]thiophen-3-yl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneAusbeute 36,3 %

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, 0.8465 mmol) was reacted with 3-bromo-benzo[b]thiophene (216.3 mg, 1.0158 mmol), 1,4-dioxane (50 mL), copper iodide (10.7 mg, 0.0865 mmol), trans-1,2-diamino cyclohexane (29 mg, 0.2539 mmol) and potassium phosphate (449.1 mg, 2.1162 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 95 mg of the product (36.3% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-60d4776c23e44f07bef89b0ce718b675
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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