Potassium Carbonate → HCID 86692593, compound

HRID 1748654Notes

Reaction equation

HRID 1748654 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10](C(N)=O)=[N:9]2)=[CH:4][CH:3]=1.C([O:19][C:20]([C:22]1([C:28]2[CH:33]=[CH:32][C:31](Br)=[CH:30][N:29]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])C.C[CH:36]([NH2:40])C(C)N.C(=O)([O-])[O-:42].[K+].[K+]>[Cu]I.O.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:36]([NH:40][C:31]3[CH:32]=[CH:33][C:28]([C:22]4([C:20]([OH:19])=[O:21])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:29][CH:30]=3)=[O:42])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 1363622,3-ButanediamineHCID 86692594HCID 86692594, compoundHCID 86692595HCID 86692595, compound

Product 1

HCID 86692593HCID 86692593, compoundYield 3.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

1-(4-Chlorophenyl)-5-methyl-1H-pyrazolecarboxamide (0.43 g), 1-(5-bromopyridin-2-yl)cyclohexanecarboxylic acid ethyl ester (0.83 g), copper (I) iodide (20 mg), 1,2-dimethylethylenediamine (0.13 g) and potassium carbonate (0.42 g) were added to 1,4-dioxane (5 ml), and stirred at 105° C. for six hours. The reaction solution was treated with water, extracted with ethyl acetate and concentrated in vacuo. 1N Aqueous solution of sodium hydroxide (5 ml) and ethanol (5 ml) were added to the residue, and stirred at 75° C. for seven hours. The solvent was evaporated, the residue was purified with a silica gel column chromatography (ethyl acetate:n-hexane=1:1) to give the titled compound (20 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated in vacuo
  3. addition1N Aqueous solution of sodium hydroxide (5 ml) and ethanol (5 ml) were added to the residue
  4. stirringstirred at 75° C. for seven hours
  5. customThe solvent was evaporated
  6. customthe residue was purified with a silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-7c923a0112484c4cb0e66af701fd46df
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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