YM-53601

9H-咔唑,2-[(2E)-2-(1-氮杂双环[2.2.2]辛-3-亚基)-2-氟乙氧基]-,一盐酸盐Chemical Name: (E)-2-[2-Fluoro-2-(quinuclidin-3-ylidene)ethoxy]-9H-carbazole hydrochloride
CAS No. 182959-33-7, 182959-28-0 (undefined isomer), 182961-13-3 (Z-isomer)
项目整合开发状态: Preclinical
项目研究机构: Yamanouchi (Originator)
合成路线:The Horner-Emmons condensation of 3-quinuclidinone (I) with triethyl 2-fluoro-2-phosphonoacetate (II) produced the unsaturated ester (III).The amino-borane complex (IV) was then obtained by treatment of (III) with borane in THF.Ester group of (IV) reduction by means of sodium bis(2-methoxyethoxy)aluminium hydride gave the allylic alcohol (V),which was converted into chloride (VI) by treatment with mesyl chloride in the presence of LiCl.Condensation of chloride (VI) with 2-hydroxycarbazole (VII) yielded ether (VIII).After acid cleavage of the amino-borane complex (VIII),the title compound was isolated as the hydrochloride salt.