1,2-Diaminocyclohexane, trans- → 1-Imidazo[1,2-a]pyridin-3-yl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-One

HRID 80151Notes

Reaction equation

HRID 80151 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].I[C:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]2=[N:17][CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[N:17]1[CH:16]=[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[CH3:1])[C:9]2=[O:13])[N:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=12

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 107527743-Iodoimidazo[1,2-a]pyridineHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361371-Imidazo[1,2-a]pyridin-3-yl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-OneYield 19.81%

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: 250 mg, 1.4108 mmol) was reacted with 3-iodo-imidazo[1,2-a]pyridine (344 mg, 1.4108 mmol), 1,4-dioxane (10 mL), copper iodide (34 mg), trans-1,2-diamino cyclohexane (68 mg) and potassium phosphate (898 mg, 4.2325 mmol) to afford the crude product. Purification by column chromatography on silica gel (10% MeOH in CHCl3) afforded 82 mg of the product (19.81% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-103d0a086d654ba0992d721950137b2e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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