N,N'-Dimethylethylenediamine → HCID 89691128, compound

HRID 2202878Notes

Reaction equation

HRID 2202878 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]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:23]([CH3:30])[C:22]=2[CH:31]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu](I)I.O.CS(C)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:18]3[CH:19]=[CH:20][C:21]4[N:25]=[C:24]([CH2:26][CH:27]([CH3:28])[CH3:29])[N:23]([CH3:30])[C:22]=4[CH:31]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 21504713HCID 21504713, compoundHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one

Product 1

HCID 89691128HCID 89691128, compoundYield 11.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (115 mg), 6-bromo-2-isobutyl-1-methyl-1H-benzimidazole (130 mg), potassium carbonate (202 mg), copper iodide (93 mg), N,N′-dimethylethylenediamine (0.052 ml) and DMSO (3 ml) was heated at 120° C. for 3 h under microwave irradiation. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The precipitate was collected by filtration, and washed with IPE and EtOAc to give the title compound (23 mg) as an off-white solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with IPE and EtOAc

Sources & evidence

ORD record
ord-6c853bbad04446e7a0d3827932cc1f9c
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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