Ciglitazone, U-63287, ADD-3878

酪里达唑Chemical Name: (?-5-[[4-[(1-Methylcyclohexyl)methoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-[4-(1-Methylcyclohexhylmethoxy)benzyl]thiazolidine-2,4-dione
CAS No. 74772-77-3
项目整合开发状态: Preclinical
项目研究机构: Takeda (Originator)
合成路线:The reaction of 1-methylcyclohexylmethanol (II) with 4-chloronitrobenzene (III) by means of NaH in hot DMSO gives 4-(1-methylcyclohexylmethoxylnitrobenzene (III),which is reduced with H2 over Pd/C in methanol yielding 4-(1-methylcyclohexylmethoxylaniline (IV).Diazotation of (IV) with NaNO2 and HCl in water affords a solution of the corresponding diazonium chloride (V),which is condensed with methyl acrylate (VI) by means of Cu2O affording methyl 2-chloro-3-[4-(1-methylcyclohexylmethoxyl)phenyl]propionate (VII).The cyclization of (VII) with thiourea (VIII) by means of sodium acetate in hot 2-methoxyethanol gives 2-imino-5-[4-(1-methylcyclohexylmethoxy)benzyl]thiazolidin-4-one (IX),which is finally hydrolyzed with HCl in refluxing 2-methoxyethanol - water.

合成路线:By cyclization of (VIII) with methyl 2-(methanesulfonyloxy)-3-[4-(1-methylcyclohexylmethoxy)phenyl]propionate (X) by means of sodium acetate in hot 2-methoxyethanol,followed by hydrolysis with HCl in ethanol water.