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 1710660Notes

Reaction equation

HRID 1710660 reaction equation
[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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-4ba38da0d3014cc5a59ceff5565e94ad
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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