Potassium Carbonate → 1-(2-Chloro-4-methyl-quinolin-6-yl)-3-pyridin-3-yl-imidazolidin-2-one

HRID 80034Notes

Reaction equation

HRID 80034 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]=[C:19]([Cl:24])[CH:18]=[C:17]2[CH3:25].N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:24][C:19]1[CH:18]=[C:17]([CH3:25])[C:16]2[C:21](=[CH:22][CH:23]=[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:15]=2)[N:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 47381436-Bromo-2-chloro-4-methylquinolineHCID 148342041-(Pyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361931-(2-Chloro-4-methyl-quinolin-6-yl)-3-pyridin-3-yl-imidazolidin-2-oneYield 35.17%

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: 95.8 mg, 0.5882 mmol) was reacted with 6-bromo-2-chloro-4-methyl-quinoline (150 mg, 0.5882 mmol), 1,4-dioxane (5 mL), copper iodide (11.2 mg, 0.05882 mmol), trans-1,2-diamino cyclohexane (20.20 mg, 0.1764 mmol) and potassium carbonate (162.6 mg, 1.1764 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 70 mg of the product (35.17% 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-434163df41434fd380fcfa00cb05700a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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