Sch-37370

N-乙酰基地氯雷他定Chemical Name: 11-(1-Acetyl-4-piperidylidene)-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine
CAS No. 117796-52-8
项目整合开发状态: Phase II
项目研究机构: Schering-Plough (Originator)
合成路线:N-tert-Butyl-3-methyl-2-pyridinecarboxamide (I) was treated with two equivalents of butyllithium at -40 C,and the resulting dianion was C-alkylated with 3-chlorobenzyl chloride (II) to provide the phenetylpyridine (III).Further refluxing with phosphoryl chloride afforded nitrile (IV),which was condensed with the piperidinyl Grignard reagent (V) to yield,after hydrolysis,ketone (VI).Acid-catalyzed cyclization of ketone (VI) produced the tricyclic compound (VII).Demethylation was then accomplished by conversion to the ethyl carbamate (VIII) by treatment with ethyl chloroformate,followed by hydrolysis to the N-unsubstituted piperidine (IX).Finally,acetylation of (IX) in the presence of pyridine provided the target amide.