1,2-Diaminocyclohexane, trans- → 1-Benzothiazol-6-yl-3-(6-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383846

Reaction equation

HRID 2383846 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[N:21][CH:22]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:17]4[CH:22]=[N:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 12010205-Bromo-2-methylpyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 596362231-Benzothiazol-6-yl-3-(6-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 51.8%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 150 mg, 0.685 mmol) was reacted with 5-bromo-2-methyl-pyridine (140.5 mg, 0.822 mmol), 1,4-dioxane (10 mL), copper iodide (12.92 mg, 0.068 mmol), trans-1,2-diamino cyclohexane (23 mg, 0.205 mmol) and potassium phosphate (435 mg, 2.055 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 110 mg of the product (51.80% 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-d92bf07a170e40d186ec07d4ffbf828c
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Linked notes

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