N,N'-Dimethylethylenediamine → HCID 89691107, compound

HRID 2202920Notes

Reaction equation

HRID 2202920 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]([CH:26]3[CH2:28][CH:27]3[C:29]([OH:32])([CH3:31])[CH3:30])[N:23]([CH3:33])[C:22]=2[CH:34]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CS(C)=O>[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]([CH:26]5[CH2:28][CH:27]5[C:29]([OH:32])([CH3:30])[CH3:31])[N:23]([CH3:33])[C:22]=4[CH:34]=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 117949767HCID 117949767, compound

Product 1

HCID 89691107HCID 89691107, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (27 mg), 2-((1RS,2SR)-2-(6-bromo-1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl)propan-2-ol (35 mg), copper iodide (21.8 mg), N,N′-dimethylethylenediamine (10.1 mg), potassium carbonate (31.7 mg) and DMSO (1 ml) was stirred at 150° C. overnight. The mixture was quenched with 28% NH3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (MeOH/EtOAc) to give the title compound (10 mg) as a pale yellow solid.

Workup

  1. customThe mixture was quenched with 28% NH3 solution at room temperature
  2. extractionextracted with EtOAc
  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 NH silica gel column chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-1e95f320a72c4a528febddd69ccd400b
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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