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

HRID 80087

Reaction equation

HRID 80087 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:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:21][C:18]1[CH:17]=[C:16]([F:22])[CH:15]=[CH:20][C:19]=1[N:10]1[CH2:11][CH2:12][N:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 676741-Bromo-2,4-difluorobenzeneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596362181-(2,4-Difluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 61.2%

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: 150 mg, 0.8474 mmol) was reacted with 1-bromo-2,4-difluoro-benzene (0.114 mL, 1.0169 mmol), 1,4-dioxane (20 mL), copper iodide (16 mg, 0.08474 mmol), trans-1,2-diamino cyclohexane (29.4 mg, 0.254 mmol) and potassium phosphate (449.7 mg, 2.118 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 150 mg of the product (61% 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-6d6c0fc43c1a471e8512af85e6a354ad
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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