1,2-Diaminocyclohexane, trans- → 1-(4-Methyl-pyridin-3-yl)-3-(3-methyl-thiophen-2-yl)-imidazolidin-2-one

HRID 80094

Reaction equation

HRID 80094 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[S:16][CH:17]=[CH:18][C:19]=1[CH3:20].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[S:16][CH:17]=[CH:18][C:19]=2[CH3:20])[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 843142-Bromo-3-methylthiopheneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596362431-(4-Methyl-pyridin-3-yl)-3-(3-methyl-thiophen-2-yl)-imidazolidin-2-oneYield 56.7%

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, 0.84 mmol) was reacted with 2-bromo-3-methyl-thiophene (150 mg, 0.84 mmol), 1,4-dioxane (10 mL), copper iodide (16 mg, 0.084 mmol), trans-1,2-diamino cyclohexane (28.8 mg, 0.25 mmol) and potassium phosphate (445 mg, 2.1 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 130 mg of the product (56.7% yield).

Workup

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

Sources & evidence

ORD record
ord-5ab74061a48646108a28612da6a9e307
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

Loading…