YM-53389

Chemical Name: (+)-2-Chloro-5-methoxy-4-[5-[piperidin-2(S)-ylmethyl]-1,2,4-oxadiazol-3-yl]phenylamine monohydrochloride
CAS No. 220850-98-6, 220850-99-7 ((R)-isomer), 174822-16-3 (free base, undefined isomer)
项目整合开发状态: Preclinical
项目研究机构: Yamanouchi (Originator)
合成路线:Benzamide (II) was prepared by treatment of the benzotriazolyl ester (I) with ammonium hydroxide in DMF.Dehydration of amide (II) with phosphorus oxychloride gave rise to nitrile (III),and subsequent addition of hydroxylamine to the cyano group of (III) furnished the N-hydroxybenzamidine (IV).Cyclization of (IV) with methyl 2-piperidineacetate (V) in the presence of NaH produced the oxadiazole compound (VI).Racemic (VI) was resolved employing L-ditoluoyltartaric acid,and the desired (S)-enantiomer was finally converted to the corresponding hydrochloride salt.