N,N'-Dimethylethylenediamine → HCID 89690917, compound

HRID 2202934Notes

Reaction equation

HRID 2202934 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:19]=[CH:20][C:21]2[N:25]=[C:24]([C:26](=[O:28])[CH3:27])[N:23]([CH3:29])[C:22]=2[CH:30]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu](I)I>[C:26]([C:24]1[N:23]([CH3:29])[C:22]2[CH:30]=[C:18]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=4)=[CH:9][C:10]3=[O:14])[CH:19]=[CH:20][C:21]=2[N:25]=1)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 83866933HCID 83866933, compound

Product 1

HCID 89690917HCID 89690917, compoundYield 1.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (596 mg), 1-(6-bromo-1-methyl-1H-benzimidazol-2-yl)ethanone (640 mg), N,N′-dimethylethylenediamine (0.272 ml), copper iodide (482 mg) and potassium carbonate (699 mg) in DMSO (10 ml) was stirred at 150° C. for 1 h. The mixture was quenched with NH3 solution and extracted with EtOAc twice. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOH to give the title compound (16.8 mg) as a white solid.

Workup

  1. customThe mixture was quenched with NH3 solution
  2. extractionextracted with EtOAc twice
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
  8. customThe resulting solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-0e8ec1744a3b46438db192a248433590
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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