1,2-Diaminocyclohexane, trans- → HCID 59636154, Verbindung

HRID 80118

Reaktionsgleichung

Reaktionsgleichung von HRID 80118
[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]=[CH:17][C:18]2[O:22][C:21]([CH3:23])=[N:20][C:19]=2[CH:24]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:23][C:21]1[O:22][C:18]2[CH:17]=[CH:16][C:15]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])=[CH:24][C:19]=2[N:20]=1

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 101045995-Bromo-2-methyl-1,3-benzoxazoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 59636154HCID 59636154, VerbindungAusbeute 16,5 %

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: 0.1 g, 0.00057 mol) was reacted with 5-bromo-2-methyl-benzooxazole (0.119 g, 0.000597 mol), 1,4-dioxane (20 mL), copper iodide (0.01 g, 0.000057 mol), trans-1,2-diamino cyclohexane (0.019 g, 0.00017 mol) and potassium phosphate (0.242 g, 0.00114 mol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3), followed by preparative HPLC afforded 29 mg of the product (16% 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-c95480e484714f6d96722391606398cd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

Verknüpfte Notizen

Wird geladen…