Cesium carbonate → 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile

HRID 896299Notes

Reaction equation

HRID 896299 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:21][C:22]1[N:26]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]2[CH:32]=[CH:33][C:34]([C:36]#[N:37])=[CH:35][C:24]=2[N:23]=1>CN(C=O)C.CCOC(C)=O>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:21][C:22]2[N:26]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]3[CH:32]=[CH:33][C:34]([C:36]#[N:37])=[CH:35][C:24]=3[N:23]=2)[C:5]1=[O:13])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 16535801-(Propan-2-yl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 223493092-(Chloromethyl)-1-isopentyl-benzimidazole-5-carbonitrile

Product 1

HCID 223493242-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrileYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-isopropyl-1,3-dihydro-benzoimidazol-2-one (0.79 g, 4.5 mmol) and Cs2CO3 (4.40 g, 13.5 mmol) in DMF (50 mL) was stirred for 30 minutes then 2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile (1.34 g, 4.5 mmol) was added and the mixture stirred for 5 h at ambient temperature. The reaction mixture was diluted with EtOAc (50 mL) and filtered. The filtrate was evaporated to dryness and the residue taken up in EtOAc (100 mL), washed with water and brine. The organic layer was dried over MgSO4 and evaporated. The residue was purified by flash chromatography (gradient, hexanes:EtOAc 3:1 to 1:1) to give 1.71 g (95%) of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile as a white solid.

Workup

  1. stirringthe mixture stirred for 5 h at ambient temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (gradient, hexanes:EtOAc 3:1 to 1:1)

Sources & evidence

ORD record
ord-2b292b75ad924b399e6d7d4241c56b9a
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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