1,2-Diaminocyclohexane, trans- → HCID 66576894, compound

HRID 523610Notes

Reaction equation

HRID 523610 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:22]=[C:21](I)[CH:20]=[C:19]([Cl:24])[N:18]=1.[C@@H]1(N)CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:21]3[CH:20]=[C:19]([Cl:24])[N:18]=[C:17]([Cl:16])[CH:22]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 117373932,6-Dichloro-4-iodopyridineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 66576894HCID 66576894, compoundYield 93.02%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 500 mg, 2.4630 mmol) was reacted with 2,6-dichloro-4-iodopyridine (810 mg, 2.9556 mmol), copper iodide (47 mg, 0.2463 mmol), trans-cyclohexane-1,2-diamine (0.089 mL, 0.7389 mmol), potassium phosphate (1.56 g, 7.3891 mmol) and 1,4-dioxane (10 mL) to afford crude product. Purification by column chromatography on silica gel (2% methanol in chloroform) afforded 800 mg of pure product (93.02% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford crude product
  3. customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record
ord-eaf819d334db4b5d8d403deeaa5a6f3f
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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