N,N'-Dimethylethylenediamine → HCID 89691247, compound

HRID 2202861Notes

Reaction equation

HRID 2202861 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]([CH:26]3[CH2:28][CH2:27]3)[N:23]([CH2:29][CH3:30])[C:22]=2[CH:31]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.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]([CH:26]5[CH2:27][CH2:28]5)[N:23]([CH2:29][CH3:30])[C:22]=4[CH:31]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 89691182HCID 89691182, compound

Product 1

HCID 89691247HCID 89691247, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (100 mg), 6-bromo-2-cyclopropyl-1-ethyl-1H-benzimidazole (124 mg), copper iodide (81 mg), N,N′-dimethylethylenediamine (0.048 ml), potassium carbonate (147 mg) and DMSO (2.5 ml) was heated 120° C. for 1 h under microwave irradiation. The mixture was quenched with 28% NH3 solution at room temperature and extracted with EtOAc. 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 solid was recrystallized from IPA/hexane to give the title compound (85 mg) as a light pink solid.

Workup

  1. customThe mixture was quenched with 28% NH3 solution at room temperature
  2. extractionextracted with EtOAc
  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 solid was recrystallized from IPA/hexane

Sources & evidence

ORD record
ord-c3d4f02e71ea4dbd8f4bd9263208aa6f
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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