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【结 构 式】

【分子编号】62867

【品名】5-ethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine; 2-(5-ethyl-2-pyridinyl)ethyl 4-nitrophenyl ether

【CA登记号】

【 分 子 式 】C15H16N2O3

【 分 子 量 】272.30372

【元素组成】C 66.16% H 5.92% N 10.29% O 17.63%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

The condensation of 2-(5-ethyl-2-pyridyl)ethanol (I) with 4-fluoronitrobenzene (II) by means of NaH in DMF gives 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene (III), which is reduced with H2 over Pd/C in methanol to yield the corresponding aniline (IV). The reaction of (IV) with NaNO2/HBr and methyl acrylate (V) in acetone/methanol affords the 2-bromopropionate derivative (VI), which is cyclized with thiourea (VII) by means of NaOAc in refluxing ethanol to provide the 2-imino-4-thiazolidinone (VIII). Finally, this compound is hydrolyzed with refluxing 2N HCl.

1 Meguro, K.; Fujita, T. (Takeda Chemical Industries, Ltd.); Thiazolidinedione derivs., their production and use. EP 0193256; ES 8705886; JP 1986267580; US 4687777 .
2 Sohda, T.; Momose, Y.; Meguro, K.; Kawamatsu, Y.; Sugiyama, Y.; Ikeda, H.; Studies on antidiabetic agents. Synthesis and hypoglycemic activity of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidinediones. Arzneim-Forsch Drug Res 1990, 40, 1, 37.
3 Prous, J.; Castaner, J.; PIOGLITAZONE HYDROCHLORIDE < Prop INNM; USAN >. Drugs Fut 1990, 15, 11, 1080.
4 Meguro, K.; Momose, Y.; Sohda, T.; Oi, S.; Ikeda, H.; Hatanaka, C.; Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds. Chem Pharm Bull 1991, 39, 6, 1440-5.
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) 14139 2-(5-Ethyl-2-pyridinyl)-1-ethanol 5223-06-3 C9H13NO 详情 详情
(II) 14153 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene 350-46-9 C6H4FNO2 详情 详情
(III) 62867 5-ethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine; 2-(5-ethyl-2-pyridinyl)ethyl 4-nitrophenyl ether C15H16N2O3 详情 详情
(IV) 62868 4-[2-(5-ethyl-2-pyridinyl)ethoxy]aniline; 4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenylamine C15H18N2O 详情 详情
(V) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(VI) 62869 methyl 2-bromo-3-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl}propanoate C19H22BrNO3 详情 详情
(VII) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VIII) 62870 5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-2-imino-1,3-thiazolidin-4-one C19H21N3O2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

 

1 R4jendra GL, Pang NG, Maya JS, et al. 2004. Improved process for preparation of thiazolidinedione derivatives. W0 2004024059
2 Sohda T, Momose Y, Meguro K, et al. 1990. Studies on antidiabetic agents Synthesis and hypoglycemic activity of 5-[4-(pyridylaIkoxy) benzyl]-2,4-thiazolidinediones. Arzneim-Forsch, 40: 37~42
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) 62866 2-(5-ethyl-2-pyridinyl)ethyl methanesulfonate C10H15NO3S 详情 详情
(II) 11236 4-Nitrophenol; p-Nitrophenol 100-02-7 C6H5NO3 详情 详情
(III) 62867 5-ethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine; 2-(5-ethyl-2-pyridinyl)ethyl 4-nitrophenyl ether C15H16N2O3 详情 详情
(IV) 62868 4-[2-(5-ethyl-2-pyridinyl)ethoxy]aniline; 4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenylamine C15H18N2O 详情 详情
(V) 66597 4-(2-(5-ethylpyridin-2-yl)ethoxy)benzenediazonium   C15H16N3O 详情 详情
(VI) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(VII) 66598 methyl 3-(4-(2-(5-ethylpyridin-2-yl)ethoxy)phenyl)propanoate   C19H23NO3 详情 详情
Extended Information