Potassium Carbonate → HCID 68789034, compound

HRID 2383752Notes

Reaction equation

HRID 2383752 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].[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12081Methyl 4-bromobenzoateHCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 68789034HCID 68789034, compoundYield 91.6%

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 4-bromo-benzoic acid methyl ester (182 mg, 0.84650 mmol), 1,4-dioxane (50 mL), copper iodide (16 mg, 0.084650 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 (5% MeOH in DCM) afforded 230 mg of 4-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl ester (91.6% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (5% MeOH in DCM)

Sources & evidence

ORD record
ord-f0c01c60f1574fc781dcc0d8beb8d8ca
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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