Potassium Carbonate → 4-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl)-benzonitrile

HRID 80063Notes

Reaction equation

HRID 80063 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:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[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:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12162Benzonitrile, 4-bromo-HCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596362594-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl)-benzonitrileYield 64.2%

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, 0.8465 mmol) was reacted with 4-bromo-benzonitrile (154 mg, 0.84650 mmol), 1,4-dioxane (50 mL), copper iodide (16 mg, 0.084650 mmol), trans-1,2-diamino cyclohexane (29 mg, 0.2539 mmol) and potassium carbonate (468 mg, 3.3860 mmol) to afford the crude product. Purification by column chromatography on silica gel (5% MeOH in DCM) afforded 151 mg of the product (64.2% yield).

Workup

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

Sources & evidence

ORD record
ord-b01412db9d4540568ef3375a4040f69f
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…