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

HRID 523533

Reaktionsgleichung

Reaktionsgleichung von HRID 523533
[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[S:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:21]1[C:17]([N:12]2[CH2:13][CH2:14][N:10]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[CH:1]3[CH2:3][CH2:2]3)[C:11]2=[O:15])=[CH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]1=2

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 947862-Bromobenzo(b)thiopheneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 665764861-(Benzo[b]thiophen-2-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-oneAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 150 mg, 0.738 mmol) was reacted with 2-bromobenzo[b]thiophene (188 mg, 0.886 mmol), 1,4-dioxane (6 mL), copper iodide (14.0 mg, 0.0739 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (10.5 mg, 0.0739 mmol) and potassium phosphate (470 mg, 2.21 mmol) to afford the crude product. Purification by column chromatography on silica gel (0.5% methanol in CHCl3) afforded 85 mg of the product (34% yield).

Aufarbeitung

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (0.5% methanol in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-86d3a76a156546209da239f34eee9091
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339501B2

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