1,2-Diaminocyclohexane, trans- → 1-(3-Acetyl-4-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80126Notes

Reaction equation

HRID 80126 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:16]=[CH:17][C:18]([F:24])=[C:19]([C:21](=[O:23])[CH3:22])[CH:20]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[C:21]([C:19]1[CH:20]=[C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])[CH:16]=[CH:17][C:18]=1[F:24])(=[O:23])[CH3:22]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 226074761-(5-Bromo-2-fluorophenyl)ethanoneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 687845751-(3-Acetyl-4-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 24.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 0.500 g, 2.82 mmol) was reacted with 1-(5-bromo-2-fluoro-phenyl)-ethanone (0.612 g, 2.82 mmol), 1,4-dioxane (30 mL), copper iodide (53.81 mg, 0.282 mmol), trans-1,2-diamino cyclohexane (97.03 mg, 0.846 mmol) and potassium phosphate (1.79 g, 8.46 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 220 mg of 1-(3-Acetyl-4-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (24.9% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-b21d23e05c7e4ea5a4c9c3810ca0fb71
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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