SP-500263

Chemical Name: 7-Hydroxy-3-phenyl-4-[4-[2-(1-piperidinyl)ethoxy]benzyl]-2H-1-benzopyran-2-one hydrochloride
CAS No. 280137-80-6 (free base)
项目整合开发状态: Preclinical
项目研究机构: Signal (Originator)
合成路线:Friedel-Crafts acylation of 3-methoxyphenol (I) with 4-hydroxyphenylacetic acid (II) in the presence of ZnCl2 and POCl3 furnished ketone (III),which was subsequently protected with triisopropylsilyl chloride and Et3N to yield the mono-silyl ether (IV).Coumarin (VI) was then synthesized by condensation of hydroxy ketone (IV) with phenylacetyl chloride (V) in the presence of K2CO3.Alkylation of the phenolic hydroxyl group of (VI) with N-(2-chloroethyl)piperidine (VII) gave the piperidinylethyl ether (VIII).Finally,selective methyl ether hydrolysis using HBr in refluxing HOAc led to the title compound.