N,N'-Dimethylethylenediamine → HCID 89702445, compound

HRID 2203036Notes

Reaction equation

HRID 2203036 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]([C:26](=[O:29])[CH2:27][CH3:28])[N:23]([CH3:30])[C:22]=2[CH:31]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[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]([C:26](=[O:29])[CH2:27][CH3:28])[N:23]([CH3:30])[C:22]=4[CH:31]=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 89691245HCID 89691245, compound

Product 1

HCID 89702445HCID 89702445, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (100 mg), 1-(6-bromo-1-methyl-1H-benzo[d]imidazol-2-yl)propan-1-one (170 mg), N,N′-dimethylethylenediamine (0.046 ml), CuI (81 mg) and potassium carbonate (176 mg) in DMSO (3 ml) was stirred at 150° C. for 30 min under N2 atmosphere. The mixture was purified by NH silica gel column chromatography (hexane/EtOAc), followed by recrystallization from IPA to give the title compound (6.1 mg) as a pale yellow solid.

Workup

  1. customThe mixture was purified by NH silica gel column chromatography (hexane/EtOAc)
  2. customfollowed by recrystallization from IPA

Sources & evidence

ORD record
ord-fd6ddb1e180e4bb1a482bbb6aaa6008e
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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