Trifluoromethanesulfonic acid → HCID 71252092, compound

HRID 2411860Notes

Reaction equation

HRID 2411860 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C:27]([CH3:29])([CH3:28])[C:26](=[O:30])[N:25](CC5C=CC(OC)=CC=5)[C:24]4=[O:40])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>ClCCCl>[CH3:1][C:2]1[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C:27]([CH3:28])([CH3:29])[C:26](=[O:30])[NH:25][C:24]4=[O:40])=[CH:19][CH:18]=3)=[O:16])[CH2:13][CH2:14]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 71252211HCID 71252211, compound

Product 1

HCID 71252092HCID 71252092, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (4-bromophenyl) [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (150 mg) described in Preparation Example 165, 3-(4-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione (119 mg) described in Preparation Example 53, cesium carbonate (260 mg) and copper(I) iodide (38 mg) were added toluene (8 mL) and N,N′-dimethylethylenediamine (43 μL), and the mixture was stirred with heating under reflux for 29 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give 1-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-3-(4-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione. The obtained 1-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-3-(4-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione was dissolved in 1,2-dichloroethane (4 mL), trifluoromethanesulfonic acid (92 μL) was added and the mixture was stirred at 80° C. for 13 hr. To the reaction mixture was added 5% aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform/methanol (10:1). The organic layer was dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol) to give the title compound (34 mg).

Workup

  1. extractionthe mixture was extracted with chloroform/methanol (10:1)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol)

Sources & evidence

ORD record
ord-7a8b96aec6fa42baa6c70e9e5f30828b
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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