N,N'-Dimethylethylenediamine → 5-chloro-N-((1-(4-(4-ethyl-2,3-dioxopiperazin-1-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 559604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559604
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[CH:13][N:14]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[CH2:23]([N:25]1[CH2:30][CH2:29][NH:28][C:27](=[O:31])[C:26]1=[O:32])[CH3:24].CNCCNC.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O1CCOCC1.[Cu]I>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[CH:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:28]4[CH2:29][CH2:30][N:25]([CH2:23][CH3:24])[C:26](=[O:32])[C:27]4=[O:31])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 1088121-Ethyl-2,3-piperazinedioneHCID 249868975-Chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

Produkt 1

HCID 247602315-chloro-N-((1-(4-(4-ethyl-2,3-dioxopiperazin-1-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamideAusbeute 13,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 (70 mg, 0.16 mmol), N-ethylpiperazine-2,3-dione (45 mg, 0.32 mmol), N,N′-dimethylethylenediamine (0.020 mL, 0.19 mmol) and K2CO3 (65 mg, 0.47 mmol) in DMSO (1 mL) and dioxane (1 mL) was degassed with Ar before being charged with CuI (20 mg, 0.10 mmol). The mixture in a sealed tube was heated at 110° C. overnight. The mixture was then purified by HPLC to give the titled compound (10 mg). MS 458.1 and 460.1 (M+H, Cl pattern).

Aufarbeitung

  1. customwas degassed with Ar
  2. customThe mixture was then purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-30218e9166b94b569d23b69c4ba06603
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063077B2

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