4-methyl-1,2-thiazolidine 1,1-dioxide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 4-methylisothiazolidine 1,1-dioxide (202 mg) described in Preparation Example 9 and [4-(5-ethyl-3-methylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (500 mg) described in Preparation Example 133 and by the reaction and treatment in the same manner as in Example 1, the title compound (46 mg) was obtained. described in Preparation Example 133 and by the reaction and treatment in the same manner as in Example 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 4-methylisothiazolidine 1,1-dioxide (270 mg) described in Preparation Example 9 and [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (421 mg) described in Preparation Example 113 and by the reaction and treatment in the same manner as in Example 4, the title compound (134 mg) was obtained. described in Preparation Example 113 and by the reaction and treatment in the same manner as in Example 4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl 4-iodobenzoate (571 mg), 4-methylisothiazolidine 1,1-dioxide (280 mg) described in Preparation Example 9, potassium carbonate (572 mg) and copper(I) iodide (197 mg) were added toluene (6 mL) and N,N′-dimethylethylenediamine (230 μL), and the mixture was stirred with heating under reflux for 9 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, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give ethyl 4-(4-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoate. The obtained ethyl 4-(4-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoate was dissolved in tetrahydrofuran (5 mL), 1N aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated from the reaction mixture, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. To the obtained residue was added diethyl ether, and the precipitate was collected by filtration to give the title compound (210 mg). with heating under reflux for 9 hr The reaction mixture was cooled the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine the solvent was evaporated The obtained residue was purified by column chromatography (hexane:ethyl acetate)