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

HRID 80085

Reaction equation

HRID 80085 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])=[C:17]([CH3:22])[CH:16]=1.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:19]=[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][C:17]=1[CH3:22]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 1235275-Bromo-2-fluorotolueneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498721471-(4-Fluoro-3-methyl-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 30%

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: 160 mg, 0.9039 mmol) was reacted with 4-bromo-1-fluoro-2-methyl-benzene (0.135 mL, 0.7142 mmol), 1,4-dioxane (15 mL), copper iodide (0.005 g, 0.0263 mmol), trans-1,2-diamino cyclohexane (0.015 g, 0.1315 mmol) and potassium phosphate (0.575 g, 2.7094 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 26 mg of the product (30% yield).

Workup

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

Sources & evidence

ORD record
ord-182259001c244b85ab85e0f98a19bc8e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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