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US 9,328,066 B2Granted
Chiral synthesis of N-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-6-methoxyphenyl}-1-[2,3-dihydroxy-propyl]cyclopropanesulfonamides
AssigneeBayer Intellectual Property GmbH
InventorsPeter Fey, Agathe Christine Mayer
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Abstract
The present invention relates to a novel enantioselective method of preparing (S)- and (R)-enantiomers of N-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-6-5 methoxyphenyl}-1-[2,3-dihydroxy-propyl]cyclopropanesulfonamide, to novel intermediate compounds, and to the use of said novel intermediate compounds for the preparation of said (S)- and (R)-enantiomers of N-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-6-methoxyphenyl}-1-[2,3-dihydroxy-propyl]cyclopropanesulfonamide.
Claims13
The compound
- 1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}cyclopropanesulfonyl bromide (S)-10-Br:
A method of preparing a compound of formula (S)-14:
- comprising:
- i) reacting a compound of formula (S)-10:
- with a compound of formula (12):
- in the presence of a bromide, optionally in the presence of a base, and optionally in a solvent,
- thereby providing a reaction mixture containing a compound of formula (S)-13:
- and, then,
- ii) adding an aqueous mineral acid to said reaction mixture containing a compound of formula (S)-13,
- thereby providing a compound of formula (S)-14.
5 more elements
A method of preparing a compound of formula (S)-14:
- comprising:
- i) reacting a compound of formula (S)-10-Br:
- with a compound of formula (12):
- optionally in the presence of a base, and optionally in a solvent,
- thereby providing a reaction mixture containing a compound of formula (S)-13:
- and, then,
- ii) adding an aqueous mineral acid to said reaction mixture containing a compound of formula (S)-13,
- thereby providing a compound of formula (S)-14.
5 more elements
Dependencies are inferred from the claim text.