1,2-Diaminocyclohexane, trans- → 1-(2-Methyl-2H-indazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80170Notes

Reaction equation

HRID 80170 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:23]=[CH:22][C:21]2[C:17](=[CH:18][N:19]([CH3:24])[N:20]=2)[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:24][N:19]1[CH:18]=[C:17]2[C:21]([CH:22]=[CH:23][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]2)=[N:20]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 115140075-Bromo-2-methyl-2H-indazoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361501-(2-Methyl-2H-indazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 6.228%

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: 100 mg, 0.564 mmol) was reacted with 5-bromo-2-methyl-2H-indazole (120 mg, 0.5741 mmol), 1,4-dioxane (15 mL), copper iodide (10 mg, 0.056 mmol), trans-1,2-diamino cyclohexane (19 mg, 0.166 mmol) and potassium phosphate (360 mg, 1.698 mmol) to afford the crude product. Purification by preparative HPLC afforded 3.6 mg of the product (6.228% yield).

Workup

  1. customto afford the crude product
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-8c05c978b6644e148af578f049ac577e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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