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

HRID 80194

Reaktionsgleichung

Reaktionsgleichung von HRID 80194
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH:23]([O:26][CH3:27])[O:24][CH3:25].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:21]4[CH:20]=[N:19][CH:18]=[CH:17][C:22]=4[CH:23]([O:26][CH3:27])[O:24][CH3:25])[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 207151453-Bromo-4-(dimethoxymethyl)pyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Produkt 1

HCID 498724521-Benzothiazol-6-yl-3-(4-dimethoxymethyl-pyridin-3-yl)-imidazolidin-2-oneAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 14, 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 590 mg, 2.7 mmol) was reacted with 3-bromo-4-dimethoxymethyl-pyridine (I-149a: 690 mg, 2.97 mmol), 1,4-dioxane (50 mL), copper iodide (51.46 mg, 0.27 mmol), trans-1,2-diamino cyclohexane (93 mg, 0.81 mmol) and potassium phosphate (1.72 g, 8.1 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 510 mg of the product (51.2% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-524b007336484208b7dfcbc140fb2626
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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