1,2-Diaminocyclohexane, trans- → 1-Benzo[b]thiophen-5-yl-3-(4-methyl-pyridin-3-yl)-1,3-dihydro-imidazol-2-one

HRID 80179

Reaktionsgleichung

Reaktionsgleichung von HRID 80179
[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:23]=[CH:22][C:18]2[S:19][CH:20]=[CH:21][C:17]=2[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:19]1[CH:20]=[CH:21][C:17]2[CH:16]=[C:15]([N:10]3[CH:11]=[CH:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])[CH:23]=[CH:22][C:18]1=2

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 27765785-Bromo-1-benzothiopheneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 498719621-Benzo[b]thiophen-5-yl-3-(4-methyl-pyridin-3-yl)-1,3-dihydro-imidazol-2-oneAusbeute 4,61 %

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: 500 mg, 2.825 mmol) was reacted with 5-bromo-benzo[b]thiophene (661.86 mg, 3.12 mmol), 1,4-dioxane (20 mL), copper iodide (53.81 g, 0.2825 mmol), trans-1,2-diamino cyclohexane (97.03 g, 0.8475 mmol) and potassium phosphate (1.796 g, 8.475 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.2% MeOH in CHCl3), followed by preparative HPLC afforded mg of the product (4.61% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.2% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-c7917739ffb44eb4944b5be3aace5382
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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