1-[(2-bromoethyl)oxy]-4-nitrobenzene; 2-bromoethyl 4-nitrophenyl ether -Drug Synthesis Database

【结构式】

【分子编号】63398

【品名】1-[(2-bromoethyl)oxy]-4-nitrobenzene; 2-bromoethyl 4-nitrophenyl ether

【CA登记号】13288-06-7

【分子式】C₈H₈BrNO₃

【分子量】246.06046

【元素组成】C 39.05% H 3.28% Br 32.47% N 5.69% O 19.51%

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：(II)

In an alternative procedure, pyrimidinone (I) is alkylated with 4-(2-bromoethoxy)nitrobenzene (II) to produce (III). Reduction of nitro compound (III) by catalytic hydrogenation affords aniline (IV). After diazotization of amine (IV), the resultant diazonium salt is coupled to ethyl acrylate in the presence of CuI, yielding the 2-bromo-3-arylpropionate (V). Cyclization of bromo ester (V) with thiourea (VI) furnishes the iminothiazolidinone (VII), which is finally hydrolyzed under acidic conditions to the target thiazolidinedione.

参考文献中间体

合成目标

【1】 Lohray, V.B.; Lohray, B.B.; Ramanujam, R.; Chakrabarti, R.; Gurram, R.M.; Paraselli, R.B.; Pakala, S.K.S. (Dr. Reddy's Research Foundation); Heterocyclic cpds., process for their preparation and pharmaceutical compsns. containing them and their use in the treatment of diabetes and related diseases. EP 0958296; US 5885997; US 5985884; US 6372750; US 6573268; WO 9741097 .

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)	63395	2-ethyl-6-methyl-4(3H)-pyrimidinone		C₇H₁₀N₂O	详情	详情
(II)	63398	1-[(2-bromoethyl)oxy]-4-nitrobenzene; 2-bromoethyl 4-nitrophenyl ether	13288-06-7	C₈H₈BrNO₃	详情	详情
(III)	63399	2-ethyl-6-methyl-3-{2-[(4-nitrophenyl)oxy]ethyl}-4(3H)-pyrimidinone		C₁₅H₁₇N₃O₄	详情	详情
(IV)	63400	3-{2-[(4-aminophenyl)oxy]ethyl}-2-ethyl-6-methyl-4(3H)-pyrimidinone		C₁₅H₁₉N₃O₂	详情	详情
(V)	63401	ethyl 2-bromo-3-[4-({2-[2-ethyl-4-methyl-6-oxo-1(6H)-pyrimidinyl]ethyl}oxy)phenyl]propanoate		C₂₀H₂₅BrN₂O₄	详情	详情
(VI)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(VII)	63402	2-ethyl-3-[2-({4-[(2-imino-4-oxo-1,3-thiazolidin-5-yl)methyl]phenyl}oxy)ethyl]-6-methyl-4(3H)-pyrimidinone		C₁₉H₂₂N₄O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVII)

参考文献中间体

合成目标

【1】 Arrowsmith JE,Cross PE,et al.1987.Processes for the preparation of N-substituted p-aminoethylsufonanilides for use as antiarryhythmic agents. EP245997

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)	12395	N-Methyl-N-(4-nitrophenethyl)amine; N-Methyl-2-(4-nitrophenyl)-1-ethanamine		C₉H₁₂N₂O₂	详情	详情
(III)	12397	N-Methyl-N-(4-nitrophenethyl)-2-(4-nitrophenoxy)-1-ethanamine; N-Methyl-N-(4-nitrophenethyl)-N-[2-(4-nitrophenoxy)ethyl]amine		C₁₇H₁₉N₃O₅	详情	详情
(IV)	12398	N-(4-Aminophenethyl)-N-[2-(4-aminophenoxy)ethyl]-N-methylamine; 4-[2-[(4-Aminophenethyl)(methyl)amino]ethoxy]aniline		C₁₇H₂₃N₃O	详情	详情
(XVII)	63398	1-[(2-bromoethyl)oxy]-4-nitrobenzene; 2-bromoethyl 4-nitrophenyl ether	13288-06-7	C₈H₈BrNO₃	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XVII)

参考文献中间体

合成目标

【1】 Cross PE, Arrowsmith JE, et aL 1990. Selective class Ⅲ antiarrhythmic agents.1.bis (arylalkyl) amines.J Med Chem, 332 1151~1155

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	12397	N-Methyl-N-(4-nitrophenethyl)-2-(4-nitrophenoxy)-1-ethanamine; N-Methyl-N-(4-nitrophenethyl)-N-[2-(4-nitrophenoxy)ethyl]amine		C₁₇H₁₉N₃O₅	详情	详情
(XVII)	63398	1-[(2-bromoethyl)oxy]-4-nitrobenzene; 2-bromoethyl 4-nitrophenyl ether	13288-06-7	C₈H₈BrNO₃	详情	详情
(XVIII)	26560	4-nitrophenethylamine	24954-67-4	C₈H₁₀N₂O₂	详情	详情
(XIX)	66270	4-Nitro-N-[2-(4-nitrophenoxy)ethyl]benzeneethanamine	226992-13-8	C₁₆H₁₇N₃O₅	详情	详情

Extended Information