1,2-Diaminocyclohexane, trans- → HCID 68787031, compound

HRID 80180Notes

Reaction equation

HRID 80180 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:31]=[CH:30][C:18]2[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:20]=[N:21][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>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][N:10]([C:15]2[CH:31]=[CH:30][C:18]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:29])[CH3:28])[N:20]=[N:21][C:17]=3[CH:16]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 68784490HCID 68784490, compound

Product 1

HCID 68787031HCID 68787031, compoundYield 83.5%

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: 175 mg, 0.9875 mmol) was reacted with 5-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzotriazole (353 mg, 1.08634 mmol), 1,4-dioxane (50 mL), copper iodide (80.76 mg, 0.09875 mmol), trans-1,2-diamino cyclohexane (33.9 mg, 0.2962 mmol) and potassium phosphate (524 mg, 2.4689 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 350 mg of 1-(4-Methyl-pyridin-3-yl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzotriazol-5-yl]-imidazolidin-2-one (79% 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-3eb43a5e00ac403d90533305946f9aea
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…