Potassium Carbonate → HCID 59636188, compound

HRID 80089Notes

Reaction equation

HRID 80089 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].C(OC([N:21]1[C:30]2[C:25](=[CH:26][C:27](Br)=[CH:28][CH:29]=2)[CH2:24][CH2:23][C:22]1=[O:32])=O)(C)(C)C.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:27]2[CH:26]=[C:25]3[C:30](=[CH:29][CH:28]=2)[NH:21][C:22](=[O:32])[CH2:23][CH2:24]3)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 687869156-bromo-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 59636188HCID 59636188, compoundYield 31.5%

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, 0.8474 mmol) was reacted with 6-bromo-2-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (276 mg, 0.8474 mmol), 1,4-dioxane (5 mL), copper iodide (16.14 mg, 0.08474 mmol), trans-1,2-diamino cyclohexane (29.1 mg, 0.2542 mmol) and potassium carbonate (234.3 mg, 1.6948 mmol) to afford the crude product. Purification by preparative HPLC afforded 86 mg of the product (31.5% yield).

Workup

  1. customto afford the crude product
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-937f232e4aa74f8086cc076e23e69f08
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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