Synthesis of pyrazinyl pyridine-3-sulfonamide compounds

Details Synthesis of pyrazinyl pyridine-3-sulfonamide compounds Synthesis of pyrazinyl pyridine-3-sulfonamide compounds

2005-09-13

2005-09-13

McKenzie, Thomas C. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

active

06943254

ABSTRACT:
A process for the manufacture of:wherein R is (1-4C)alkyl, carboxyl(1-4C)alkyl or 1,3,4-oxadiazol-2-yl comprises:(a) reaction of the diazonium salt of 3-amino-2-chloropyridine with thionyl chloride in water and an electron transfer catalyst;(b) reaction with isobutyl-(3-methoxy-5-methylpyrazin-2-yl)carbamate and an alkali metal hydride in inert solvent; and(I) where R is (1-4C)alkyl, carboxy(1-4C)alkyl:(c) reaction with a boronic acid:(or an anhydride or ester therof) in the presence of a base and a palladium or nickel catalyst in solvent; and removal of the isobutoxy carbonyl group; or(ii) where R is 1,3,4-oxadiazol-2-yl(c) reaction with 4-methoxycarbonylphenylboronic acid (or an anhydride or ester thereof) with a source fluoride ion under aqueous conditions;(d) removal of the isobutoxycarbonyl protecting group;(e) conversion of the methyl ester group to the hydrazide; and(f) conversion to a 1,3,4-oxadiazol-2-yl moiety.

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