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

HRID 80114Notes

Reaction equation

HRID 80114 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].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 203456994-Fluoro-4'-iodo-1,1'-biphenylHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361871-(4'-Fluoro-biphenyl-4-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 12.35%

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: 100 mg, 0.5649 mmol) was reacted with 4′-fluoro-4-iodo-biphenyl (198 mg, 0.675 mmol), 1,4-dioxane (15 mL), copper iodide (0.0096 g, 0.0504 mmol), trans-1,2-diamino cyclohexane (0.0032 g, 0.0280 mmol) and potassium phosphate (0.359 g, 1.691 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in CHCl3), followed by preparative HPLC afforded 12 mg of the product (12.35% yield).

Workup

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

Sources & evidence

ORD record
ord-a7d674e0371a4a5e97121160a54b9f6a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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