N-(3-Bromophenyl)acetamide → N-{3-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-phenyl}-acetamide

HRID 80093Notes

Reaction equation

HRID 80093 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]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][N:10]([C:15]2[CH:16]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 12123N-(3-Bromophenyl)acetamideHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 59636210N-{3-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-phenyl}-acetamideYield 23%

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 N-(3-bromo-phenyl)-acetamide (217.6 mg, 1.0169 mmol), 1,4-dioxane (20 mL), copper iodide (16 mg, 0.08474 mmol), trans-1,2-diamino cyclohexane (449.7 mg, 0.2542 mmol) and potassium phosphate (29.4 mg, 2.1185 mmol) to afford the crude product. Purification by column chromatography on silica gel (5% MeOH in CHCl3), followed by preparative HPLC afforded 60 mg of the product (23% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-930d824f080a4a2f8cfc821f0998e69e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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