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【结 构 式】

【分子编号】34178

【品名】2-imino-5-[4-[(1-methylcyclohexyl)methoxy]benzyl]-1,3-thiazolidin-4-one

【CA登记号】

【 分 子 式 】C18H24N2O2S

【 分 子 量 】332.46684

【元素组成】C 65.03% H 7.28% N 8.43% O 9.62% S 9.64%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

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.

1 Kawamatsu, Y.; Mizuno, K.; Sugiyama, Y.; Imamiya, E.; Fujita, T.; Sohda, T.; Studies on antidiabetic agents. II. Synthesis of 5-[4-(1-methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione (ADD-3878) and its derivatives. Chem Pharm Bull 1982, 30, 10, 3580.
2 Nohria, V.; Castaner, J.; Serradell, M.N.; Ciglitazone. Drugs Fut 1984, 9, 4, 258.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 34173 (1-methylcyclohexyl)methanol C8H16O 详情 详情
(II) 13909 1-Chloro-4-nitrobenzene; p-Nitrochlorobenzene 100-00-5 C6H4ClNO2 详情 详情
(III) 34174 1-[(1-methylcyclohexyl)methoxy]-4-nitrobenzene; (1-methylcyclohexyl)methyl 4-nitrophenyl ether C14H19NO3 详情 详情
(IV) 34175 4-[(1-methylcyclohexyl)methoxy]phenylamine; 4-[(1-methylcyclohexyl)methoxy]aniline C14H21NO 详情 详情
(V) 34176 4-[(1-methylcyclohexyl)methoxy]benzenediazonium chloride C14H19ClN2O 详情 详情
(VI) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(VII) 34177 methyl 2-chloro-3-[4-[(1-methylcyclohexyl)methoxy]phenyl]propanoate C18H25ClO3 详情 详情
(VIII) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(IX) 34178 2-imino-5-[4-[(1-methylcyclohexyl)methoxy]benzyl]-1,3-thiazolidin-4-one C18H24N2O2S 详情 详情
Extended Information