Sodium Iodide → 5-[2-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)ethoxy]-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 333729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333729
[OH:1][C:2]1[C:3](=[O:20])[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[N:5][N:6]([CH3:8])[CH:7]=1.Cl[CH2:22][CH2:23][N:24]1[C:28]2=[N:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:27]2[CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(N(C)C)=O>[N:24]1([CH2:23][CH2:22][O:1][C:2]2[C:3](=[O:20])[C:4]([C:9]3[N:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:12]=[CH:11][CH:10]=3)=[N:5][N:6]([CH3:8])[CH:7]=2)[C:28]2=[N:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:27]2[CH2:26][CH2:25]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 7619001-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazoleHCID 895867365-hydroxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Produkt 1

HCID 566541295-[2-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)ethoxy]-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 5-hydroxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (201 mg), 1-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (249 mg), cesium carbonate (428 mg) and sodium iodide (253 mg) in dimethylacetamide (10 mL) was stirred at 80° C. for 13 hr. The reaction mixture was filtered to separate an insoluble material, which was washed with ethyl acetate. The filtrate and washing were combined, and the mixture was concentrated under reduced pressure to dryness. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) to give the title compound (227 mg) as a white solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto separate an insoluble material, which
  3. washwas washed with ethyl acetate
  4. washThe filtrate and washing
  5. concentrationthe mixture was concentrated under reduced pressure to dryness
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-b17b7a1c89c044c99d5b74bf888da079
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883788B2

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