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【结 构 式】

【分子编号】63402

【品名】2-ethyl-3-[2-({4-[(2-imino-4-oxo-1,3-thiazolidin-5-yl)methyl]phenyl}oxy)ethyl]-6-methyl-4(3H)-pyrimidinone

【CA登记号】

【 分 子 式 】C19H22N4O3S

【 分 子 量 】386.47484

【元素组成】C 59.05% H 5.74% N 14.5% O 12.42% S 8.3%

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:(VII)

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.

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
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