1,2-Diaminocyclohexane, trans- → 3-Benzothiazol-6-yl-4-methyl-1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80279Notes

Reaction equation

HRID 80279 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:14]([CH3:15])[CH2:13][NH:12][C:11]3=[O:16])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].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[CH:14]([CH3:15])[CH2:13][N:12]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][C:23]=4[CH3:24])[C:11]3=[O:16])[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 144235133-Iodo-4-methylpyridineHCID 596361921-Benzothiazol-6-yl-5-methyl-imidazolidin-2-one

Product 1

HCID 498729323-Benzothiazol-6-yl-4-methyl-1-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 24.15%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-5-methyl-imidazolidin-2-one (I-203b: 150 mg, 0.644 mmol) was reacted with 3-iodo-4-methyl-pyridine (140.99 mg, 0.644 mmol), 1,4-dioxane (10 mL), copper iodide (12.27 mg, 0.0644 mmol), trans-1,2-diamino cyclohexane (27.43 mg, 0.193 mmol) and potassium phosphate (341 mg, 1.61 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% MeOH in DCM) afforded 50 mg of the product (24.15% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% MeOH in DCM)

Sources & evidence

ORD record
ord-063105cce20049a0a30165b63a9236eb
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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