Potassium Carbonate → 1-Naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80105

Reaction equation

HRID 80105 reaction equation
N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].Br[C:16]1[CH:17]=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[N:36]1[CH2:40][CH2:39][NH:38][C:37]1=[O:41]>CCCCCC.[Cu](I)I.C(OCC)(=O)C.O1CCOCC1>[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[N:36]1[CH2:40][CH2:39][N:38]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=2)[C:37]1=[O:41]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 111279913-Bromo-5-(trifluoromethyl)pyridineHCID 596361671-Naphthalen-2-yl-imidazolidin-2-one

Product 1

HCID 596362161-Naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-oneYield 52%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Copper iodide (12.6 mg, 0.066 mmol), trans-1,2-diamino cyclohexane (22.79 mg, 0.199 mmol) and potassium carbonate (183.5 mg, 1.32 mmol) were added to 1,4-dioxane (5 mL) and 3-bromo-5-trifluoromethyl-pyridine (150 mg, 0.66 mmol) previously degassed with argon (10 minutes). The reaction was purged with argon for a further 10 minutes, followed by the addition of 1-naphthalen-2-yl-imidazolidin-2-one (I-79b: 140 mg, 0.66 mmol) and the resulting mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was filtered through celite and the bed was washed with chloroform. The organic layer was dried over Na2O4 and concentrated. Purification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant) afforded 120 mg (52% yield) of 1-naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one.

Workup

  1. custompreviously degassed with argon (10 minutes)
  2. customThe reaction was purged with argon for a further 10 minutes
  3. temperaturethe resulting mixture was heated
  4. filtrationThe reaction mixture was filtered through celite
  5. washthe bed was washed with chloroform
  6. customThe organic layer was dried over Na2O4
  7. concentrationconcentrated
  8. customPurification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant)

Sources & evidence

ORD record
ord-b4701bd379cf4461a06ebbf58e991c9b
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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