Potassium Carbonate → 1-Ethyl-6-(2-oxo-3-pyridin-3-yl-imidazolidin-1-yl)-3,4-dihydro-1H-quinolin-2-one

HRID 2383709Notes

Reaction equation

HRID 2383709 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]([CH2:24][CH3:25])[C:19](=[O:26])[CH2:18][CH2:17]2.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH2:24]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([N:9]3[CH2:10][CH2:11][N:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[C:8]3=[O:12])=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]1=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneHCID 669113046-Bromo-1-ethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 596362671-Ethyl-6-(2-oxo-3-pyridin-3-yl-imidazolidin-1-yl)-3,4-dihydro-1H-quinolin-2-oneYield 47.71%

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: 95 mg, 0.5882 mmol) was reacted with 6-bromo-1-ethyl-3,4-dihydro-1H-quinolin-2-one (150 mg, 0.5882 mmol), 1,4-dioxane (5 mL), copper iodide (11 mg, 0.05882 mmol), trans-1,2-diamino cyclohexane (10 mg, 0.08823 mmol) and potassium carbonate (162 mg, 1.1764 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform), afforded 94 mg of the product (47.71% 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-abd58a7095524f42b23d234e65cbba52
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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