Potassium Carbonate → HCID 59636207, compound

HRID 2383727Notes

Reaction equation

HRID 2383727 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:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:25][CH3:26])[C:20](=[O:27])[CH:19]=[C:18]2[CH3:28].N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH2:25]([N:21]1[C:22]2[C:17](=[CH:16][C:15]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])=[CH:24][CH:23]=2)[C:18]([CH3:28])=[CH:19][C:20]1=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 68784278HCID 68784278, compound

Product 1

HCID 59636207HCID 59636207, compoundYield 28.1%

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: 99 mg, 0.5597 mmol) was reacted with 6-bromo-1-ethyl-4-methyl-1H-quinolin-2-one (150 mg, 0.5597 mmol), 1,4-dioxane (5 mL), copper iodide (10.66 mg, 0.05597 mmol), trans-1,2-diamino cyclohexane (19.22 mg, 0.1679 mmol) and potassium carbonate (77.37 mg, 1.1194 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 56 mg of the product (28.1% 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-29f0bc99b69c43d7ade36da9102950b6
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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