Process for preparing antiviral compound
AssigneeAbbVie Inc.
InventorsJean-Christophe Califano, James J. Napier, Calvin L. Becker, Su Yu
Life of this patent
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Abstract
This invention is directed to: (a) processes for preparing a compound and salts thereof that, inter alia, are useful for inhibiting hepatitis C virus (HCV); (b) intermediates useful for the preparation of the compound and salts; (c) pharmaceutical compositions comprising the compound or salts; and (d) methods of use of such compositions.
Claims19
A compound or salt thereof, wherein the compound corresponds in structure to compound (4) or compound (8):
A process for preparing N-(4-((3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)ethynyl)phenyl)methanesulfonamide (compound 6) comprising:
- reacting N-(4-ethynylphenyl)methanesulfonamide (compound 5) with compound 3, wherein compound 3 is selected from the group consisting of 1-(3-tert-butyl-5-iodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (compound 3a), 1-(3-bromo-5-tert-butyl-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (compound 3b), and 1-(3-tert-butyl-5-chloro-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (compound 3c) thus forming N-(4-((3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)ethynyl)phenyl)methanesulfonamide (compound 6):
- wherein R2 is chlorine, bromine or iodine.
A process for preparing N-(4-((3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)ethynyl)phenyl)methanesulfonamide (compound 6) comprising:
- reacting 1-(3-tert-butyl-5-ethynyl-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (compound 4) with compound 2, wherein compound 2 is selected from the group consisting of N-(4-iodophenyl)methanesulfonamide (compound 2a), N-(4-bromophenyl)methanesulfonamide (compound 2b), N-(4-chlorophenyl)methanesulfonamide (compound 2c), N-(4-[(arylsulfonyl)oxy]phenyl)methanesulfonamide (compound 2d), and N-(4-[(perfluoroalkylsulfonyl)oxy]phenyl)methanesulfonamide (compound 2e) in the presence of a catalyst, a base and a solvent:
- wherein R1 is selected from the group consisting of iodine, bromine, chlorine, arylsulfonyloxy and perfluoroalkylsulfonyloxy.
Dependencies are inferred from the claim text.