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

HRID 80163

Reaction equation

HRID 80163 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]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]([F:26])([F:25])[F: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[CH2:14][CH2:13][N:12]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][C:22]=4[C:23]([F:26])([F:25])[F:24])[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 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 498723561-Benzothiazol-6-yl-3-(4-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-oneYield 12.04%

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, 0.684 mmol) was reacted with 3-bromo-4-trifluoromethyl-pyridine (185.75 mg, 0.822 mmol), 1,4-dioxane (10 mL), copper iodide (12.99 mg, 0.0684 mmol), trans-1,2-diamino cyclohexane (23.37 mg, 0.205 mmol) and potassium phosphate (435 mg, 2.052 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in CHCl3), followed by preparative HPLC afforded 7 mg of the product (12.04% 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-535264ea86a441f281b9f18678908f26
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

Loading…