Potassium Carbonate → HCID 58097290, compound

HRID 1514751Notes

Reaction equation

HRID 1514751 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17](I)[CH:16]=[CH:15][C:3]=1[O:4][Si:5]([CH:12]([CH3:14])[CH3:13])([CH:9]([CH3:11])[CH3:10])[CH:6]([CH3:8])[CH3:7].[C:20]([C:24]1[CH:28]=[C:27]([NH2:29])[NH:26][N:25]=1)([CH3:23])([CH3:22])[CH3:21].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[C:20]([C:24]1[CH:28]=[C:27]([NH2:29])[N:26]([C:17]2[CH:16]=[CH:15][C:3]([O:4][Si:5]([CH:12]([CH3:14])[CH3:13])([CH:9]([CH3:11])[CH3:10])[CH:6]([CH3:8])[CH3:7])=[C:2]([Cl:1])[CH:18]=2)[N:25]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 58097282HCID 58097282, compoundHCID 178441179HCID 178441179, compound

Product 1

HCID 58097290HCID 58097290, compoundYield 65.8%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
111 °C

Procedure

To a solution of aryl iodide of Example 1 (493.6 g, 1.202 moles) in toluene (1000 ml) under nitrogen, was added 3-tert-butyl-1H-pyrazol-5-amine (184.2 g, 1.322 moles) followed by trans-N,N′dimethylcyclohexane-1,2-diamine (16.2 g, 0.240 moles), potassium carbonate (348 g, 2.52 moles) and copper (I) iodide (11.6 g, 0.061 moles). The mixture was heated at 111° C. for 16 hours. After this time the reaction was cooled to 20° C., and partitioned with water (1500 ml) and ethyl acetate (1500 ml). The organic phase was sequentially washed with 10% w/v aqueous citric acid solution (1500 ml) and water (1500 ml). Solvent was distilled under reduced pressure and replaced by n-heptane (1500 ml). The solution was cooled to 5° C. granulated for 16 hours. The solid was collected by filtration to give the title compound as a brown solid (334 g, 65%).

Workup

  1. temperatureAfter this time the reaction was cooled to 20° C.
  2. custompartitioned with water (1500 ml) and ethyl acetate (1500 ml)
  3. washThe organic phase was sequentially washed with 10% w/v aqueous citric acid solution (1500 ml) and water (1500 ml)
  4. distillationSolvent was distilled under reduced pressure
  5. temperatureThe solution was cooled to 5° C.
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-95bb97d55770413cac0aa0fb8653c27c
Source dataset
uspto-grants-2012_07
Patent number
US08222273B2

Reaction notes

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