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

HRID 80273Notes

Reaction equation

HRID 80273 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:6][N:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[CH3:13])[C:4](=[O:14])[NH:3]1.I[C:17]1[CH:25]=[CH:24][C:20]2[N:21]=[CH:22][S:23][C:19]=2[CH:18]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:23]1[C:19]2[CH:18]=[C:17]([N:3]3[C:2]([CH3:15])([CH3:1])[CH2:6][N:5]([C:7]4[CH:8]=[N:9][CH:10]=[CH:11][C:12]=4[CH3:13])[C:4]3=[O:14])[CH:25]=[CH:24][C:20]=2[N:21]=[CH:22]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 226090026-Iodo-1,3-benzothiazoleHCID 596361394,4-Dimethyl-1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 498728423-Benzothiazol-6-yl-4,4-dimethyl-1-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 12.14%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

4,4-Dimethyl-1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-163b: 150 mg, 0.731 mmol) was reacted with 6-iodo-benzothiazole (I-200e: 248 mg, 0.950 mmol), 1,4-dioxane (10 mL), copper iodide (13 mg, 0.0682 mmol), trans-1,2-diamino cyclohexane (31 mg, 0.218 mmol) and potassium phosphate (387 mg, 1.825 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 30 mg of the product (12.14% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

Sources & evidence

ORD record
ord-9936d77650d74f4183c2c68b43a4afe7
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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