Cesium carbonate → 5-Chloro-1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-3-methyl-1,3-dihydro-benzoimidazol-2-one

HRID 1710660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710660
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.Cl[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([O:30][CH3:31])[CH:24]=2)[CH2:19][CH2:18]1)=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH2:14][C:15]([N:17]3[CH2:18][CH2:19][N:20]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([O:30][CH3:31])[CH:24]=4)[CH2:21][CH2:22]3)=[O:16])[C:8](=[O:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 140429442H-Benzimidazol-2-one,6-chloro-1,3-dihydro-1-methyl-(9CI)HCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanone

Produkt 1

HCID 160596335-Chloro-1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-3-methyl-1,3-dihydro-benzoimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-1-methyl-1,3-dihydro-benzoimidazol-2-one (61) (75 mg, 0.41 mmol, 1 eq), 2-Chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (125 mg, 0.41 mmol, 1 eq), cesium carbonate (401 mg, 1.23 mmol, 3 eq) in DMF (2 ml) was stirred at rt overnight. The reaction solution was diluted with ethyl acetate, washed with water. The organic layer was evaporated to dryness and the crude residue was purified by flash chromatography to provide the desired product 5-chloro-1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-3-methyl-1,3-dihydro-benzoimidazol-2-one (62): LCMS observed for (M+H)+: 449.2.

Aufarbeitung

  1. washwashed with water
  2. customThe organic layer was evaporated to dryness
  3. customthe crude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ba38da0d3014cc5a59ceff5565e94ad
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790726B2

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