1,2-Diaminocyclohexane, trans- → 1-m-Tolyl-3-(4-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80169

Reaktionsgleichung

Reaktionsgleichung von HRID 80169
[C:1]1([CH3:13])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:2]=1.Br[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[C:1]1([CH3:13])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][N:9]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[C:21]([F:24])([F:23])[F:22])[C:8]2=[O:12])[CH:2]=1

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 43049911-(Meta-tolyl)-2-imidazolidinoneHCID 199372633-Bromo-4-(trifluoromethyl)pyridine

Produkt 1

HCID 596362611-m-Tolyl-3-(4-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-oneAusbeute 34,43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 14, 1-m-tolyl-imidazolidin-2-one (I-131b: 150 mg, 0.8522 mmol) was reacted with 3-bromo-4-trifluoromethyl-pyridine (160 mg, 0.8522 mmol), 1,4-dioxane (5 mL), copper iodide (16.23 mg, 0.08522 mmol), trans-1,2-diamino cyclohexane (29.27 mg, 0.2552 mmol) and potassium phosphate (542.56 mg, 2.556 mmol) to afford the crude product. Purification by preparative HPLC afforded 94 mg of the product (34.43% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a1bcd68890a641bc8110f29bde673d23
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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