Potassium Carbonate → 1-Pyridin-3-yl-3-quinolin-6-yl-imidazolidin-2-one

HRID 80029

Reaction equation

HRID 80029 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:2]=1.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][N:9]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][CH:18]=[CH:17]4)[C:8]2=[O:12])[CH:2]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 792436-BromoquinolineHCID 148342041-(Pyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361801-Pyridin-3-yl-3-quinolin-6-yl-imidazolidin-2-oneYield 60.09%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 1, 1-pyridin-3-yl-imidazolidin-2-one (I-1b: 117 mg, 0.7215 mmol) was reacted with 6-bromo-quinoline (150 mg, 0.7215 mmol), 1,4-dioxane (5 mL), copper iodide (13 mg, 0.07215 mmol), trans-1,2-diamino cyclohexane (24.78 mg, 0.21645 mmol) and potassium carbonate (199.49 mg, 1.1443 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform), afforded 125 mg of the product (60.09% 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-6e8278ff0aab434080fa66146aafd0ed
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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