Potassium Carbonate → 1-(4-Methyl-pyridin-3-yl)-3-quinolin-2-yl-imidazolidin-2-one

HRID 80046

Reaction equation

HRID 80046 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].Cl[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N: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:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596362091-(4-Methyl-pyridin-3-yl)-3-quinolin-2-yl-imidazolidin-2-oneYield 40.8%

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, 0.84650 mmol) was reacted with 2-chloro-quinoline (138.4 mg, 0.84650 mmol), 1,4-dioxane (30 mL), copper iodide (16 mg, 0.08465 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 (2% MeOH in DCM) afforded 105 mg of the product (40.8% yield).

Workup

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

Sources & evidence

ORD record
ord-cd1f6569dce04606845e6c1692ff336e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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