1,2-Diaminocyclohexane, trans- → HCID 49872454, compound

HRID 2383871Notes

Reaction equation

HRID 2383871 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:20]=[CH:19][N:18]2[C:21]([Cl:24])=[CH:22][N:23]=[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:21]1[N:18]2[CH:19]=[CH:20][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])=[CH:16][C:17]2=[N:23][CH:22]=1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 687846147-Bromo-3-chloro-imidazo[1,2-a]pyridine

Product 1

HCID 49872454HCID 49872454, compoundYield 6.57%

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: 165 mg, 0.932 mmol) was reacted with 7-bromo-3-chloro-imidazo[1,2-a]pyridine (278 mg, 1.21 mmol), 1,4-dioxane (6 mL), copper iodide (17.71 mg, 0.093 mmol), trans-1,2-diamino cyclohexane (32.01 mg, 0.279 mmol) and potassium phosphate (493.96 mg, 2.33 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3), followed by preparative HPLC afforded 20 mg of the product (6.57% 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-f91fc82e516d483c99853e64f60df8aa
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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