Fluorinated 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 fluorinated heterocyclic compounds, including monofluoroflosequinan and difluoroflosequinan. The methods of the present invention comprise the synthesis of monofluoroflosequinan and difluoroflosequinan.
Claims13
A composition comprising 7-fluoro-3-fluoromethylsulfinyl-1-methyl-4-quinolone.
A composition comprising monofluoroflosequinan, said monofluoroflosequinan having the structure:
- 10
A method, comprising:
- a) providing:
- i) 7-fluoro-3-fluoromethylthio-1-methyl-4-quinolone and ii) m-chloroperbenzoic acid (MCPBA);
- and
- b) reacting said 7-fluoro-3-fluoromethylthio-1-methyl-4-quinolone and m-chloroperbenzoic acid in a solvent under conditions such that 7-fluoro-3-fluoromethylsulfinyl-1-methyl-4-quinolone is produced.
A method, comprising
- a) providing:
- i) 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone (flosequinan), and ii) (diethylamino)sulfur trifluoride (DAST);
- and
- b) reacting said 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone (flosequinan), and (diethylamino)sulfur trifluoride in a solvent under conditions such that 7-fluoro-3-fluoromethylthio-1-methyl-4-quinolone is produced.
A composition comprising 3-difluoromethylsulfinyl-7-fluoro-1-methyl-4-quinolone.
A composition comprising difluoroflosequinan, said difluoroflosequinan having the structure:
- 11
A method, comprising:
- a) providing:
- i) 7-fluoro-3-fluoromethylthio-1-methyl-4-quinolone, ii) SELECTFLUOR and iii) triethylamine and
- b) reacting said 7-fluoro-3-fluoromethylthio-1-methyl-4-quinolone, SELECTFLUOR and triethylamine in a solvent under conditions such that 3-difluoromethylthio-7-fluoro-1-methyl-4-quinolone is produced;
- and
- c) further reacting said 3-difluoromethylthio-7-fluoro-1-methyl-4-quinolone with m-chloroperbenzoic acid (MCPBA) in a solvent under conditions such that 3-difluoromethylsulfinyl-7-fluoro-1-methyl-4-quinolone is produced.
Dependencies are inferred from the claim text.