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

HRID 2383868Notes

Reaction equation

HRID 2383868 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:14]=[CH:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH3:23].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]=[CH:13][N:12]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][C:22]=4[CH3:23])[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 144235133-Iodo-4-methylpyridineHCID 687851061-Benzothiazol-6-yl-1,3-dihydro-imidazol-2-one

Product 1

HCID 498719631-Benzothiazol-6-yl-3-(4-methyl-pyridin-3-yl)-1,3-dihydro-imidazol-2-oneYield 6.63%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-benzothiazol-6-yl-1,3-dihydro-imidazol-2-one (I-142b: 170 mg, 0.7834 mmol) was reacted with 3-iodo-4-methyl-pyridine (172 mg, 0.7834 mmol), 1,4-dioxane (10 mL), copper iodide (17 mg), trans-1,2-diamino cyclohexane (34 mg) and potassium phosphate (499 mg, 2.3502 mmol) to afford the crude product. Purification by column chromatography on silica gel (2-3% MeOH in CHCl3), followed by preparative HPLC afforded 16 mg of the product (6.63% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2-3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-74ef3365366445e0ada40975289892ce
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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