N,N'-Dimethylethylenediamine → HCID 89691290, compound

HRID 2202872Notes

Reaction equation

HRID 2202872 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]([C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[N:23]([CH3:31])[C:22]=2[CH:32]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu](I)I>[CH:28]1([C:26]([C:24]2[N:23]([CH3:31])[C:22]3[CH:32]=[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)=[O:27])[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 121386244HCID 121386244, compound

Product 1

HCID 89691290HCID 89691290, compoundYield 16.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (236 mg), (6-bromo-1-methyl-1H-benzimidazol-2-yl)(cyclopropyl)methanone (300 mg), N,N′-dimethylethylenediamine (0.115 ml), copper iodide (205 mg) and potassium carbonate (594 mg) in DMSO (3 ml) was stirred at 150° C. for 1 h. The mixture was purified by NH silica gel column chromatography (hexane/EtOAc). The obtained solid was washed with water and IPE to give the title compound (76 mg) as a yellow solid.

Workup

  1. customThe mixture was purified by NH silica gel column chromatography (hexane/EtOAc)
  2. washThe obtained solid was washed with water and IPE

Sources & evidence

ORD record
ord-8ee2e9d6aaeb4f559229d0c73f9e7f2b
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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