1,2-Diaminocyclohexane, trans- → 2-Imidazolidinone,1-(5-benzothiazolyl)-3-(4-methyl-3-pyridinyl)-

HRID 80088Notes

Reaction equation

HRID 80088 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].I[C:15]1[CH:16]=[CH:17][C:18]2[S:22][CH:21]=[N:20][C:19]=2[CH:23]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:22]1[C:18]2[CH:17]=[CH:16][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:23][C:19]=2[N:20]=[CH:21]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 190067695-Iodo-1,3-benzothiazoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596362362-Imidazolidinone,1-(5-benzothiazolyl)-3-(4-methyl-3-pyridinyl)-Yield 70.6%

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: 150 mg, 0.84650 mmol) was reacted with 5-iodo-benzothiazole (221 mg. 0.84650 mmol), 1,4-dioxane (25 mL), copper iodide (16 mg, 0.084650 mmol), trans-1,2-diamino cyclohexane (29 mg, 0.2539 mmol) and potassium phosphate (538 mg, 2.539 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 185 mg of the product (70.6% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in DCM)

Sources & evidence

ORD record
ord-b78201ce41b44cdcab5d3db21eafe981
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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