Ethyl Acetate → (4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

HRID 33187Notes

Reaction equation

HRID 33187 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].Cl.[N:22]1([C:28]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[S:30][N:29]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(OCC)(=O)C>C(#N)C>[S:30]1[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:28]([N:22]2[CH2:23][CH2:24][N:25]([C:10]([C:9]3[CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=3[O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[O:12])[CH2:26][CH2:27]2)=[N:29]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 58863351(S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acid

Product 1

HCID 11577135(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared in analogy to example 1.1 b) from 5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (Example 2.7) and 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (CA=87691-88-1) in acetonitrile. Chromatography (SiO2; ethyl acetate) yields the title compound as a colorless solid.

Sources & evidence

ORD record
ord-ef1b474d9b7741ccadc97eaa3ee0baa0
Source dataset
uspto-grants-2008_09
Patent number
US07429585B2

Reaction notes

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