Sodium Iodide → 1-(Cyclopropylmethyl)-5-(2-(2,3-Dihydro-1h-Imidazo[1,2-A]benzimidazol-1-Yl)ethoxy)-3-(1-Phenyl-1h-Pyrazol-5-Yl)pyridazin-4(1h)-One

HRID 333733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333733
[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([OH:11])[C:8](=[O:12])[C:7]([C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:16]=[CH:15][CH:14]=3)=[N:6]2)[CH2:3][CH2:2]1.Cl[CH2:25][CH2:26][N:27]1[C:31]2=[N:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[N:30]2[CH2:29][CH2:28]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(N(C)C)=O>[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([O:11][CH2:25][CH2:26][N:27]3[C:31]4=[N:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[N:30]4[CH2:29][CH2:28]3)[C:8](=[O:12])[C:7]([C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:16]=[CH:15][CH:14]=3)=[N:6]2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 7619001-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazoleHCID 895865391-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Produkt 1

HCID 566541311-(Cyclopropylmethyl)-5-(2-(2,3-Dihydro-1h-Imidazo[1,2-A]benzimidazol-1-Yl)ethoxy)-3-(1-Phenyl-1h-Pyrazol-5-Yl)pyridazin-4(1h)-OneAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 1-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (231 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 and an insoluble material was separated and washed with ethyl acetate. The filtrate and the washing were combined, and concentrated under reduced pressure to dryness. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) to give the title compound (231 mg) as a white amorphous powder.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customan insoluble material was separated
  3. washwashed with ethyl acetate
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-9509177f140b41a781c4c27e390e6b49
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883788B2

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