Dofequidar fumarate, MS-209

Chemical Name: 5-[3-[4-(2,2-Diphenylacetyl)piperazin-1-yl]-2-hydroxypropoxy]quinoline sesquifumarate; 1-[4-(2,2-Diphenylacetyl)piperazin-1-yl]-3-(quinoliln-5-yloxy)-2-propanol sesquifumarate; 1-(Diphenylacetyl)-4-[(2RS)-2-hydroxy-3-(5-quinolyloxy)propyl]piperazine sesquifumarate
CAS No. 153653-30-6 ((E)-2-butenedioate salt (1:1)), 153653-33-9 ((R)-isomer), 153653-31-7 ((S)-isomer), 129716-58-1 (free base)
项目整合开发状态: Phase III
项目研究机构: Mitsui Pharmaceuticals (Originator), Nihon Schering (Originator), Schering AG (Originator)
合成路线:N-(2,2-Diphenylacetyl)piperazine (IV) was prepared by acylation of N-formylpiperazine (II) with 2,2-diphenylacetyl chloride (I),followed by acid-promoted formyl deprotection of the resulting amide (III).Condensation of 5-hydroxyquinoline (VI) with epichlorohydrin (V) in the presence of potassium tert-butoxide in DMF at 90 C provided 5-(2,3-epoxypropoxy)quinoline (VII),which was subsequently coupled with acylpiperazine (IV) in boiling isopropanol to yield (VIII).This was finally treated with fumaric acid (IX) in MeOH to furnish the title sesquifumarate salt.