XR-11211

Chemical Name: (Z,Z)-8-[4-[3,6-Dioxo-5-[4-(thien-2-ylcarboxamido)benzylidene]piperazin-2-ylidenemethyl]phenoxy]octanoic acid
CAS No. 386212-69-7
项目整合开发状态: Biological Testing
项目研究机构: Xenova (Originator)
合成路线:The precursor aldehyde (VI) was prepared as follows.4-Nitrobenzaldehyde (I) was protected as the ethylene acetal (II) and subsequently reduced by catalytic hydrogenation in the presence of PtO2 to furnish aniline (III).Acylation of (III) with 2-thiophenecarbonyl chloride (IV) provided amide (V).The ethylene acetal group of (V) was then hydrolyzed to the target aldehyde (VI) under acidic conditions.

合成路线:The intermediate aldehyde (IX) was synthesized by alkylation of the sodium salt of 4-hydroxybenzaldehyde (VII) with methyl 8-bromooctanoate (VIII).

合成路线:Dioxopiperazine (X) was diacetylated in refluxing acetic anhydride to yield (XI).Aldol condensation of (XI) with the precursor aldehyde (VI) using potassium tert-butoxide in THF gave the mono-arylidene piperazine (XII).Further condensation of (XII) with the intermediate aldehyde (IX) in the presence of Cs2CO3 in DMF furnished the deacetylated bis-arylidene piperazine (XIII).The methyl ester group of (XIII) was finally hydrolyzed to the title carboxylic acid using NaOH in H2O/MeOH/THF.