1,2-Diaminocyclohexane, trans- → 1-(4-Chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383807Notes

Reaction equation

HRID 2383807 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:23][C:22]2[CH:21]=[CH:20][N:19]=[C:18]([Cl:24])[C:17]=2[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:24][C:18]1[C:17]2[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])[S:23][C:22]=2[CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 177503902-Bromo-4-chlorothieno(3,2-c)pyridineHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498718701-(4-Chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 22.16%

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: 100 mg, 0.5643 mmol) was reacted with 2-bromo-4-chloro-thieno[3,2-c]pyridine (141.3 mg, 0.5643 mmol), 1,4-dioxane (20 mL), copper iodide (10.75 mg, 0.05643 mmol), trans-1,2-diamino cyclohexane (19.38 mg, 0.1693 mmol) and potassium phosphate (299 mg, 1.4108 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 43 mg of the product (22.16% yield).

Workup

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

Sources & evidence

ORD record
ord-a54e87356fa241f69ef3f139413eda81
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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