1,2-Diaminocyclohexane, trans- → 1-(4-Methyl-3-pyridinyl)-3-(7-quinolinyl)-2-imidazolidinone

HRID 80269Notes

Reaction equation

HRID 80269 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:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[N:22]2)=[CH:17][CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[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]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[CH:17][CH:16]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 5212597-BromoquinolineHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498728431-(4-Methyl-3-pyridinyl)-3-(7-quinolinyl)-2-imidazolidinoneYield 65.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-(4-Methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b:116 mg, 0.6554 mmol) was reacted with 7-bromo-quinoline (150 mg, 0.72098 mmol), 1,4-dioxane (50 mL), copper iodide (12.4 mg, 0.06554 mmol), trans-1,2-diamino cyclohexane (22.5 mg, 0.19638 mmol) and potassium phosphate (347.3 g, 1.6365 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 130 mg of the product (65.3% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-19f6a68e8d184941a74c47bc2ee3a54f
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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