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【结 构 式】

【药物名称】

【化学名称】 

【CA登记号】

【 分 子 式 】C27H34N2O5S

【 分 子 量 】498.64643

【开发单位】

【药理作用】0

合成路线1

The condensation of 5-(benzyloxy)-2,2,4,6,7-pentamethyl-3,4-dihydrobenzofuran-3-ylmethyl methanesulfonate (I) with 2-(methylamino)ethanol (II) by heating at 120 C gives the tertiary amine (III), which is treated with SOCl2 in benzene yielding the chloroethylamino compound (IV). The condensation of (IV) with 4-nitrophenol (V) by means of K2CO3 in hot DMF affords the 4-nitrophenoxy compound (VI), which is reduced with H2 over Pd/C in ethyl acetate to the corresponding 4-aminophenoxy compound (VII). The condensation of (VII) with ethyl acrylate (VIII) by means of NaNO2 and HBr in methanol/water gives the 2-bromopropionic ester (IX), which is cyclized with thiourea (X) by means of NaOAc in refluxing ethanol yielding the thiazolidinedione (XI). Finally, this compound is debenzylated with HCl in hot acetic acid.

1 Casturi, S.R.; Lohray, V.B.; Kallam, A.R.; Pingali, H.; Ramanujam, R.; Alla, S.R. (Dr. Reddy's Research Foundation); Cpds. having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5925656 .
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) 26455 5-(benzyloxy)-2,2,4,6,7-pentamethyl-3-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-2,3-dihydro-1-benzofuran C24H32O3S 详情 详情
(II) 13324 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol 109-83-1 C3H9NO 详情 详情
(III) 26456 2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]-1-ethanol C24H33NO3 详情 详情
(IV) 26457 N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-2-chloro-N-methyl-1-ethanamine C24H32ClNO2 详情 详情
(V) 11236 4-Nitrophenol; p-Nitrophenol 100-02-7 C6H5NO3 详情 详情
(VI) 26458 N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-N-methyl-2-(4-nitrophenoxy)-1-ethanamine C30H36N2O5 详情 详情
(VII) 26459 4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]aniline C30H38N2O3 详情 详情
(VIII) 10164 ethyl acrylate 140-88-5 C5H8O2 详情 详情
(IX) 26460 ethyl 3-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]phenyl)-2-bromopropanoate C35H44BrNO5 详情 详情
(X) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(XI) 26461 5-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]benzyl)-1,3-thiazolidine-2,4-dione C34H40N2O5S 详情 详情

合成路线2

The condensation of the chloromethylamino intermediate (IV) with 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (XII) by means of NaH in in hot DMF gives the previously reported intermediate (XI), which is finally deprotected with HCl in acetic acid as before.

1 Casturi, S.R.; Lohray, V.B.; Kallam, A.R.; Pingali, H.; Ramanujam, R.; Alla, S.R. (Dr. Reddy's Research Foundation); Cpds. having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5925656 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 26457 N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-2-chloro-N-methyl-1-ethanamine C24H32ClNO2 详情 详情
(XI) 26461 5-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]benzyl)-1,3-thiazolidine-2,4-dione C34H40N2O5S 详情 详情
(XII) 26462 5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione 74772-78-4 C10H9NO3S 详情 详情
Extended Information