N,N'-Dimethylethylenediamine → HCID 89691057, compound

HRID 2202865Notes

Reaction equation

HRID 2202865 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][CH2:30][CH3:31])[C:22]=2[CH:32]=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][CH2:30][CH3:31])[C:22]=4[CH:32]=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 896910626-bromo-2-cyclopropyl-1-propyl-1H-benzimidazole

Product 1

HCID 89691057HCID 89691057, compoundYield 11%

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 (50 mg, 0.21 mmol), 6-bromo-2-cyclopropyl-1-propyl-1H-benzimidazole (65.2 mg, 0.23 mmol), copper iodide (40.4 mg, 0.21 mmol), N,N′-dimethylethylenediamine (0.024 ml, 0.21 mmol), potassium carbonate (73.3 mg, 0.53 mmol) and DMSO (1.5 ml) was heated at 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 EtOAc/hexane to give the title compound (10 mg) as an off-white 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 EtOAc/hexane

Sources & evidence

ORD record
ord-5b25af9266ef414bb0a3bb18327ae56d
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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