Chlorinated heterocyclic compounds and methods of synthesis
AssigneeR.T. Alamo Ventures I, LLC
InventorsStefan Kwiatkowski, Miroslaw Golinski
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Abstract
Compositions of the present invention comprise chlorinated heterocyclic compounds, including racemic monochloroflosequinan, purified enantiomers of monochloroflosequinan and the sulfone derivative of monochloroflosequinan. The methods of the present invention comprise the synthesis of racemic monochloroflosequinan and derivatives thereof, including the sulfone derivative. Intermediates in the synthesis are also provided. The methods further comprise the synthesis of enantiomers of monochloroflosequinan.
Claims26
A composition comprising racemic 3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone.
A composition comprising (S)-(+)-3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone in enantiomeric excess.
A composition comprising (R)-(−)-3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone in enantiomeric excess.
A composition comprising 3-chloromethylsulfonyl-7-fluoro-1-methyl-4-quinolone.
A composition comprising 3-chloromethylthio-7-fluoro-1-methyl-4-quinolone.
A method, comprising:
- a) providing:
- i) flosequinan, and
- ii) triphenyl phosphine;
- and
- b) reacting said flosequinan and triphenyl phosphine in an organic solvent under conditions such that desoxyflosequinan (7-fluoro-1-methyl-3-methylthio-4-quinolone) is produced;
- and
- c) further reacting said desoxyflosequinan with N-chlorosuccinimide and 2,2′-azobisisobutyronitrile in an organic solvent under conditions such that chlorodesoxyflosequinan (3-chloromethylthio-7-fluoro-1-methyl-4-quinolone) is produced.
A method, comprising:
- a) providing:
- i) flosequinan,
- ii) thionyl chloride, and
- iii) pyridine;
- and
- b) reacting said flosequinan, thionyl chloride and pyridine in an organic solvent under conditions such that chlorodesoxyflosequinan (3-chloromethylthio-7-fluoro-1-methyl-4-quinolone) is produced.
A method, comprising:
- a) providing:
- i) chlorodesoxyflosequinan (3-chloromethylthio-7-fluoro-1-methyl-4-quinolone),
- ii) hydrogen peroxide, and
- iii) potassium carbonate;
- and
- b) reacting said chlorodesoxyflosequinan, hydrogen peroxide and potassium carbonate in a solvent under conditions such that monochloroflosequinan (3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone) is produced.
A method, comprising:
- a) providing:
- i) flosequinan, and
- ii) N-chlorosuccinimide;
- and
- b) reacting said flosequinan and N-chlorosuccinimide in an organic solvent under conditions such that monochloroflosequinan (3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone) is produced.
A method, comprising:
- a) providing:
- i) chlorodesoxyflosequinan (3-chloromethylthio-7-fluoro-1-methyl-4-quinolone), and
- ii) a camphor based reagent;
- and
- b) reacting said chlorodesoxyflosequinan and camphor based reagent in an organic solvent under conditions such that an enantiomer of monochloroflosequinan is produced in enantiomeric excess.
A method, comprising:
- a) providing:
- i) monochloroflosequinan (3-chloromethylsulfinyl-7-fluoro-1-methyl-4-quinolone), and
- ii) m-chloroperoxybenzoic acid;
- and
- b) reacting said monochloroflosequinan and m-chloroperoxybenzoic acid in an organic solvent under conditions such that monochloroflosequinan sulfone (3-chloromethylsulfonyl-7-fluoro-1-methyl-4-quinolone) is produced.
Dependencies are inferred from the claim text.