N,N'-Dimethylethylenediamine → HCID 89691284, compound

HRID 2202853Notes

Reaction equation

HRID 2202853 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]([CH2:26][CH:27]3[CH2:29][CH2:28]3)[N:23]([CH3:30])[C:22]=2[CH:31]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CS(C)=O>[CH:27]1([CH2:26][C:24]2[N:23]([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)[CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 89690919HCID 89690919, compound

Product 1

HCID 89691284HCID 89691284, compoundYield 37%

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 (91 mg), 6-bromo-2-(cyclopropylmethyl)-1-methyl-1H-benzimidazole (165 mg), N,N′-dimethylethylenediamine (0.045 ml)-, copper iodide (79 mg), potassium carbonate (229 mg) and DMSO (3 ml) was heated at 150° C. for 2 h under microwave irradiation. After cooling, the reaction mixture was purified by NH silica gel column chromatography (hexane/EtOAc to MeOH/EtOAc). The resulting solid was washed with EtOAc and dried to give the title compound (62 mg) as a pale yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified by NH silica gel column chromatography (hexane/EtOAc to MeOH/EtOAc)
  3. washThe resulting solid was washed with EtOAc
  4. customdried

Sources & evidence

ORD record
ord-22241966042640eebf1bb82df60cdaab
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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