• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】14163

【品名】2-[5-[(Methoxymethoxy)methyl]-2-pyridinyl]-1-ethanol

【CA登记号】

【 分 子 式 】C10H15NO3

【 分 子 量 】197.23404

【元素组成】C 60.9% H 7.67% N 7.1% O 24.34%

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:(XV)

c) Synthesis of metabolite M-V: The reduction of 6-methylpyridine-3-carboxylic acid methyl ester (XII) with LiAlH4 in THF gives the corresponding hydroxymethyl derivative (XIII), which is protected with chloromethyl methyl ether as before yielding the methoxymethoxymethyl compound (XIV). Hydroxymethylation of (XIV) with formaldehyde as described affords the ethanol derivative (XV), which is condensed with 4-fluoronitrobenzene (V) as before giving 5-(hydroxymethyl)-2-[2-(4-nitrophenoxy)ethyl]pyridine (XVI). The deprotection of (XVI) with HCl in refluxing methanol yields the hydroxymethyl compound (XVII), which is treated with SOCl2 in refluxing chloroform to afford the chloromethyl compound (XVIII). The reaction of (XVIII) with KCN in hot DMF gives the corresponding cyanomethyl derivative (XIX), which by reduction of the NO2 group with H2 over Pd/C in ethyl acetate yields the amino derivative (XX). The diazotation of (XX) with NaNO2 in aqueous HBr followed by condensation with methyl acrylate as before affords the 2-bromopropionate (XXI), which is cyclized with thiourea (X) as reported to give iminothiazolidinone derivative (XXII). Finally, the hydrolysis of the cyano gives Metabolite M-V.

1 Momose, Y.; Sohda, T.; Meguro, K.; Hatanaka, C.; Ikeda, H.; Oi, S.; Studies on antidiabetic agents: Synthesis and biological activities of pioglitazone and related compounds. 11th Symp Med Chem (Dec 4-5, Tokushima) 1990, Abst P-11.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
M-V 63863 2-[6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-3-pyridinyl]acetic acid C19H18N2O5S 详情 详情
(V) 14153 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene 350-46-9 C6H4FNO2 详情 详情
(VIII) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(X) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(XII) 14160 methyl 6-methylnicotinate 5470-70-2 C8H9NO2 详情 详情
(XIII) 14161 (6-Methyl-3-pyridinyl)methanol C7H9NO 详情 详情
(XIV) 14162 Methoxymethyl (6-methyl-3-pyridinyl)methyl ether; 5-[(Methoxymethoxy)methyl]-2-methylpyridine C9H13NO2 详情 详情
(XV) 14163 2-[5-[(Methoxymethoxy)methyl]-2-pyridinyl]-1-ethanol C10H15NO3 详情 详情
(XVI) 14164 5-[(Methoxymethoxy)methyl]-2-[2-(4-nitrophenoxy)ethyl]pyridine; 2-[5-[(Methoxymethoxy)methyl]-2-pyridinyl]ethyl 4-nitrophenyl ether C16H18N2O5 详情 详情
(XVII) 14165 [6-[2-(4-Nitrophenoxy)ethyl]-3-pyridinyl]methanol C14H14N2O4 详情 详情
(XVIII) 14166 2-[5-(Chloromethyl)-2-pyridinyl]ethyl 4-nitrophenyl ether; 5-(Chloromethyl)-2-[2-(4-nitrophenoxy)ethyl]pyridine C14H13ClN2O3 详情 详情
(XIX) 14167 2-[6-[2-(4-Nitrophenoxy)ethyl]-3-pyridinyl]acetonitrile C15H13N3O3 详情 详情
(XX) 14168 2-[6-[2-(4-Aminophenoxy)ethyl]-3-pyridinyl]acetonitrile C15H15N3O 详情 详情
(XXI) 14169 methyl 2-bromo-3-(4-[2-[5-(cyanomethyl)-2-pyridinyl]ethoxy]phenyl)propanoate C19H19BrN2O3 详情 详情
(XXII) 14170 2-[6-(2-[4-[(2-Imino-4-oxo-1,3-thiazolan-5-yl)methyl]phenoxy]ethyl)-3-pyridinyl]acetonitrile C19H18N4O2S 详情 详情
Extended Information