HMN-214

(E)-4-[2-[2-[N-乙酰基-N-[(4-甲氧基苯基)磺酰]氨基]苯基]乙烯基]吡啶 1-氧化物Chemical Name: (E)-N-Acetyl-4-methoxy-N-[2-[2-(1-oxidopyridin-4-yl)vinyl]phenyl]benzenesulfonamide
CAS No. 173529-46-9
项目整合开发状态: Phase I
项目研究机构: Nippon Shinyaku (Originator), Ivax (Licensee)
合成路线:Wittig reaction between 2-nitrobenzyltriphenylphosphonium bromide (I) and pyridine-4-carboxaldehyde (II) provided the olefin adduct (IIIa-b) as a mixture of geometric isomers.After,nitro group reduction employing SnCl2,the desired E-isomer (VII),was isolated from the reaction mixture by fractional crystallization.In an alternative approach to intermediate (VII),condensation between 2-nitrobenzaldehyde (IV) and 4-picoline (V) in refluxing acetic anhydride furnished the E-olefin (VI),which was subsequently reduced with SnCl2 to the desired aniline (VII).Acylation of amine (VII) with 4-methoxybenzenesulfonyl chloride (VIII) in pyridine gave sulfonamide (IX).Subsequent oxidation of the pyridine ring to the corresponding N-oxide (X) was accomplished by treatment with peracetic acid at 70 C.The sulfonamide N was finally acetylated in boiling acetic anhydride.