Potassium Phosphate, Tribasic → 1-(Benzo[b]thiophen-5-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one

HRID 523531

Reaktionsgleichung

Reaktionsgleichung von HRID 523531
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.Br[C:17]1[CH:25]=[CH:24][C:20]2[S:21][CH:22]=[CH:23][C:19]=2[CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I>[S:21]1[CH:22]=[CH:23][C:19]2[CH:18]=[C:17]([N:12]3[CH2:13][CH2:14][N:10]([C:5]4[CH:6]=[N:7][CH:8]=[CH:9][C:4]=4[CH:1]4[CH2:3][CH2:2]4)[C:11]3=[O:15])[CH:25]=[CH:24][C:20]1=2

Komponenten

6

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 27765785-Bromo-1-benzothiopheneHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 665764841-(Benzo[b]thiophen-5-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-oneAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 83717Copper iodideKatalysator

Versuchsvorschrift

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 70 mg, 0.344 mmol) was reacted with 5-bromobenzo[b]thiophene (88.1 mg, 0.413 mmol) 1,4-dioxane (5 mL), copper iodide (6.5 mg, 0.034 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (4.8 mg, 0.034 mmol) and potassium phosphate (219 mg, 1.034 mmol) to afford the crude product. Purification by preparative HPLC afforded 15 mg of the product (13% yield).

Aufarbeitung

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-127d44b311584c0091f99dbe43c11676
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339501B2

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