N,N'-Dimethylethylenediamine → HCID 89691148, compound

HRID 2202903Notes

Reaction equation

HRID 2202903 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](=[O:28])[CH3:27])[N:23]([CH3:29])[C:22]=2[CH:30]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu](I)I>[C:26]([C:24]1[N:23]([CH3:29])[C:22]2[CH:30]=[C:18]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][C:10]3=[O:14])[CH:19]=[CH:20][C:21]=2[N:25]=1)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 83866933HCID 83866933, compound

Product 1

HCID 89691148HCID 89691148, compoundYield 9.8%

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 (312 mg), 1-(6-bromo-1-methyl-1H-benzimidazol-2-yl)ethanone (360 mg), N,N′-dimethylethylenediamine (0.141 ml), copper iodide (250 mg) and potassium carbonate (393 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 resulting solid was recrystallized from EtOH/IPA to give the title compound (54.6 mg) as a pale orange solid.

Workup

  1. customThe mixture was purified by NH silica gel column chromatography (hexane/EtOAc)
  2. customThe resulting solid was recrystallized from EtOH/IPA

Sources & evidence

ORD record
ord-0ba596123e474d0aad9868350370f8bf
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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