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    • 5. 发明授权
    • Synthesis of pyrazinyl pyridine-3-sulfonamide compounds
    • 吡嗪基吡啶-3-磺酰胺化合物的合成
    • US06943254B2
    • 2005-09-13
    • US10348229
    • 2003-01-22
    • Philip John Hogan
    • Philip John Hogan
    • C07D213/71C07B45/04C07C303/02C07C309/86C07C309/89C07D401/12C07D241/22
    • C07D401/12C07C303/02Y02P20/55C07C309/86C07C309/89
    • 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.
    • 一种制备方法:其中R是(1-4C)烷基,羧基(1-4C)烷基或1,3,4-恶二唑-2-基包括:(a)3-氨基的重氮盐 -2-氯吡啶与亚硫酰氯在水中的电子转移催化剂; (b)与惰性溶剂中的异丁基 - (3-甲氧基-5-甲基吡嗪-2-基)氨基甲酸酯和碱金属氢化物反应; 和(I)其中R是(1-4C)烷基,羧基(1-4C)烷基:(c)在碱和钯或镍的存在下与硼酸(或酸酐或酯基)反应: 溶剂中的催化剂; 并除去异丁氧基羰基; 或(ii)其中R是1,3,4-恶二唑-2-基(c)在含水条件下与4-氟甲基羰基苯基硼酸(或其酸酐或酯)与源氟离子反应; (d)除去异丁氧羰基保护基; (e)甲酯转化为酰肼; 和(f)转化为1,3,4-恶二唑-2-基部分。