1,2-Diaminocyclohexane, trans- → 1-(Isothiazol-4-yl)-3-(4 ethylpyridin-3-yl)imidazolidin-2-one

HRID 80199Notes

Reaction equation

HRID 80199 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]=[N:17][S:18][CH:19]=1.N[C@@H:21]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:18]1[CH:19]=[C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH2:1][CH3:21])[C:9]2=[O:13])[CH:16]=[N:17]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 52003584-Bromo-isothiazoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 687887131-(Isothiazol-4-yl)-3-(4 ethylpyridin-3-yl)imidazolidin-2-oneYield 172.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as described in example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.847 mmol) was reacted with 4-bromo-isothiazole (166 mg, 1.016 mmol), 1,4-dioxane (15 mL), copper iodide (16.09 mg, 0.0847 mmol), trans-1,2-diamino cyclohexane (29 mg, 0.254 mmol) and potassium phosphate (540 mg, 2.541 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 120 mg of the product (54.54% yield).

Workup

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

Sources & evidence

ORD record
ord-550eade37b7a4fcfbd1733b8d6a6c462
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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