N,N'-Dimethylethylenediamine → HCID 86661387, compound

HRID 1630664Notes

Reaction equation

HRID 1630664 reaction equation
Br[C:2]1[CH2:3][N:4](C(OCC)=O)[N:5]([C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=1.[F:19][C:20]([F:38])([F:37])[C:21]1[CH:22]=[C:23]([N:31]2[CH2:35][CH2:34][NH:33][C:32]2=[O:36])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1.CN[CH2:41][CH2:42]NC.[C:45](=O)([O-:47])[O-:46].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[F:38][C:20]([F:19])([F:37])[C:21]1[CH:22]=[C:23]([N:31]2[CH2:35][CH2:34][N:33]([C:3]3[CH:2]=[C:6]([C:45]([O:47][CH2:41][CH3:42])=[O:46])[N:5]([C:7]4[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][N:8]=4)[N:4]=3)[C:32]2=[O:36])[CH:24]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:26]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 66659283HCID 66659283, compoundHCID 86658336HCID 86658336, compound

Product 1

HCID 86661387HCID 86661387, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

600 mg (1.76 mmol) of ethyl 4-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-2-carboxylate and 527 mg (1.76 mmol) of 1-[3,5-bis(trifluoromethyl)phenyl]imidazolidin-2-one were initially charged in 30 ml of toluene, and 40.4 mg (0.21 mmol) of copper(I) iodide, 31.2 mg (0.35 mmol) of N,N′-dimethylethylenediamine and 489 mg (3.53 mmol) of potassium carbonate were added successively at room temperature. The reaction mixture was stirred under reflux for 10 h. The solvent was then distilled off, the residue was taken up in ethyl acetate and the solution was washed in each case once with water and saturated sodium chloride solution, dried over sodium sulphate and concentrated using a rotary evaporator. The desired product was isolated by chromatographic purification.

Workup

  1. temperatureunder reflux for 10 h
  2. distillationThe solvent was then distilled off
  3. washthe solution was washed in each case once with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-cb518c3fa38e4156a8be07af9374c99f
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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