N,N'-Dimethylethylenediamine → HCID 89690923, compound

HRID 2202860Notes

Reaction equation

HRID 2202860 reaction equation
[F: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>[CH:26]1([C:24]2[N:23]([CH2:29][CH3:30])[C:22]3[CH:31]=[C:18]([N:11]4[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]5[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=5)=[CH:9][C:10]4=[O:14])[CH:19]=[CH:20][C:21]=3[N:25]=2)[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 89691182HCID 89691182, compound

Product 1

HCID 89690923HCID 89690923, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (100 mg), 6-bromo-2-cyclopropyl-1-ethyl-1H-benzimidazole (133 mg), copper iodide (87 mg), N,N′-dimethylethylenediamine (0.051 ml), potassium carbonate (158 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 and THF. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc). The solid was crystallized from IPA-hexane to give the title compound (113 mg) as an off-white solid.

Workup

  1. customThe mixture was quenched with 28% NH3 solution at room temperature
  2. extractionextracted with EtOAc and THF
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)
  8. customThe solid was crystallized from IPA-hexane

Sources & evidence

ORD record
ord-d7c8c837d9e54a31bf8d4e5bd8b08221
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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