1,2-Diaminocyclohexane, trans- → Cfg-920

HRID 80084Notes

Reaction equation

HRID 80084 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].[Cl:14][C:15]1[CH:20]=[C:19](I)[CH:18]=[CH:17][N:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:14][C:15]1[CH:20]=[C:19]([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])[CH:18]=[CH:17][N:16]=1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 15165112-Chloro-4-iodopyridineHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 49871869Cfg-920Yield 83%

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: 600 mg, 3.3898 mmol) was reacted with 2-chloro-4-iodo-pyridine (974 mg, 4.067 mmol), 1,4-dioxane (60 mL), copper iodide (65 mg, 0.3398 mmol), trans-1,2-diamino cyclohexane (0.12 mL, 1.0169 mmol) and potassium phosphate (2.15 g, 10.1694 mmol) to afford 810 mg of the product (83% yield).

Sources & evidence

ORD record
ord-c9b1bae272354fee9fdb18ec9b27920a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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