Hydrogen chloride-ethyl acetate → HCID 71252265, compound

HRID 2411515Notes

Reaction equation

HRID 2411515 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@H:27]([CH3:28])[CH2:26][CH2:25][S:24]4(=[O:30])=[O:29])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[ClH:31].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:31].[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@H:27]([CH3:28])[CH2:26][CH2:25][S:24]4(=[O:30])=[O:29])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71252266(R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

Product 1

HCID 71252265HCID 71252265, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (848 mg) described in Preparation Example 113, (R)-3-methylisothiazolidine 1,1-dioxide (272 mg) described in Preparation Example 2, potassium carbonate (555 mg) and copper(I) iodide (192 mg) were added toluene (4 mL) and N,N′-dimethylethylenediamine (0.20 mL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, the mixture was extracted with chloroform, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give (R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]methanone. The obtained (R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]methanone (453 mg) was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate (0.26 mL) was added, and the precipitate was collected by filtration to give the title compound (372 mg).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-41e7363d301748fd8635ad975f809f2f
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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