2-(5-ethyl-2-pyridinyl)ethyl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】62866

【品名】2-(5-ethyl-2-pyridinyl)ethyl methanesulfonate

【CA登记号】

【分子式】C₁₀H₁₅NO₃S

【分子量】229.30004

【元素组成】C 52.38% H 6.59% N 6.11% O 20.93% S 13.98%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(III)

This compound has been obtained by several different methods. The reaction of 2-(5-ethyl-2-pyridyl)ethanol (I) with Ts-Cl and NaOH in THF gives the corresponding tosylate (II), which is condensed with 4-hydroxybenzaldehyde (IV) by means of BnNBu3Cl and NaOH or K2CO3 to yield the aryl ether (V) (1-3). The condensation of (V) with thiazolidine-2,4-dione (VI) in refluxing ethanol affords the 5-benzylidenethiazolidinedione (VII), which is finally reduced with H2 over Pd/C in DMF or dioxane. The reaction of 2-(5-ethyl-2-pyridyl)ethanol (I) with Ms-Cl and TEA in dichloromethane THF gives the corresponding mesylate (III), which is condensed with 4-hydroxybenzaldehyde (IV) by means of K2CO3 to yield the already reported aryl ether (V). The condensation of 2-(5-ethyl-2-pyridyl)ethanol (I) with 4-fluorobenzonitrile (VIII) by means of NaH gives 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzonitrile (IX), which is reduced with RaNi and HCOOH to yield the already reported 4-ethoxybenzaldehyde derivative (V).

参考文献中间体

合成目标

【1】 Saito, Y.; Yamashita, M.; Mizufune, H. (Takeda Chemical Industries, Ltd.); Process for preparing 4-(2-(2-pyridyl)ethoxy)benzaldehyde derivs.. EP 0816340 .
【2】 Mizuno, Y.; Arita, M. (Takeda Chemical Industries, Ltd.); Method for producing ethers. EP 0506273 .
【3】 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)	62865	2-(5-ethyl-2-pyridinyl)ethyl 4-methylbenzenesulfonate		C₁₆H₁₉NO₃S	详情	详情
(III)	62866	2-(5-ethyl-2-pyridinyl)ethyl methanesulfonate		C₁₀H₁₅NO₃S	详情	详情
(IV)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(V)	14141	4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzaldehyde		C₁₆H₁₇NO₂	详情	详情
(VI)	10883	1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione	2295-31-0	C₃H₃NO₂S	详情	详情
(VII)	14143	5-((E)-[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methylidene)-1,3-thiazolane-2,4-dione	144809-28-9	C₁₉H₁₈N₂O₃S	详情	详情
(VIII)	14144	4-Fluorobenzonitrile	1194-02-1	C₇H₄FN	详情	详情
(IX)	14145	4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzonitrile		C₁₆H₁₆N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【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

合成路线3

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【1】 Adiyrunan M, Guner D, Yurdakul A, et al. 2003. Ap rocess for the production of 5-[4-[2-(5-ethyl-2-pyridylethoxy) benzyl]-2,4-thiazolidinedione hydrochloride. W0 2004000810
【2】 Edward HJ. 1993. A reduction method for substituted 5-methylene-thiazoliclinediones. W0 9313095
【3】 Ulliard M, Derrien Y, Pintus T. 2002. Method for preparing compounds derived from thiazolidinedione, oxazolidinedione or hydantoin. W0 200206457

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)	62866	2-(5-ethyl-2-pyridinyl)ethyl methanesulfonate		C₁₀H₁₅NO₃S	详情	详情
(III)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(IV)	14141	4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzaldehyde		C₁₆H₁₇NO₂	详情	详情
(V)	10883	1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione	2295-31-0	C₃H₃NO₂S	详情	详情
(VI)	14143	5-((E)-[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methylidene)-1,3-thiazolane-2,4-dione	144809-28-9	C₁₉H₁₈N₂O₃S	详情	详情

Extended Information