1,2-Diaminocyclohexane, trans- → N-{5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-pyridin-2-yl}-acetamide

HRID 2383784Notes

Reaction equation

HRID 2383784 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]([NH:21][C:22](=[O:24])[CH3:23])=[N: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]=[CH:17][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[N:19][CH:20]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 2930972-Acetamido-5-bromopyridineHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 68784517N-{5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-pyridin-2-yl}-acetamideYield 40%

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, 0.8465 mmol) was reacted with N-(5-bromo-pyridin-2-yl)-acetamide (217.4 mg, 1.016 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 105 mg of the product (40% 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-fc9499ece45f4b1085f15c502a490920
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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