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【结 构 式】 
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【分子编号】24146 【品名】4-[4-(1H-imidazol-1-yl)-2-thienyl]-3-methyl-4-oxobutyric acid 【CA登记号】 |
【 分 子 式 】C12H12N2O3S 【 分 子 量 】264.30496 【元素组成】C 54.53% H 4.58% N 10.6% O 18.16% S 12.13% |
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：(V)The reaction of 4-bromo-2-thiophienecarboxaldehyde (I) with imidazole yields 4-(1H-imidazol-1-yl)-2 thiophenecarboxaldehyde (II), which by cyanide-catalyzed conjugate addition to 2-butenenitrile (III) in DMF is converted to 4-[4-(1H-imidazol-1-yl)-2-thienyl]-3-methyl-4-oxobutyronitrile (IV). Hydrolysis of (IV) in refluxing 4N HCl gives 4-[4-(1H imidazol-1-yl)-2-thienyl-4 oxobutanoic acid (V), which is finally cyclized with hydrazine in refluxing water to afford motapizone.
| 【1】 Borbe, H.; Doppelfeld, I.-S.; Hilboll, G.; Lohr, J.P.; Prop, G. (A. Nattermann & Cie. GmbH); Imidazolylalkylthienyl tetrahydropyridazines and processes for their use. DE 3241102; EP 0112987; US 4644998 . |
| 【2】 Prop, G.; Hilboll, G.; Borbe, H.O.; Motapizone. Drugs Fut 1986, 11, 1, 24. |
| 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) | 24142 | 4-bromo-2-thiophenecarbaldehyde | 18791-75-8 | C5H3BrOS | 详情 | 详情 |
| (II) | 24143 | 4-(1H-Imidazol-1-yl)-2-thiophenecarbaldehyde; 4-(1H-Imidazol-1-yl)-2 thiophenecarboxaldehyde | C8H6N2OS | 详情 | 详情 | |
| (III) | 24144 | (E)-2-butenenitrile | 4786-20-3 | C4H5N | 详情 | 详情 |
| (IV) | 24145 | 4-[4-(1H-imidazol-1-yl)-2-thienyl]-3-methyl-4-oxobutanenitrile | C12H11N3OS | 详情 | 详情 | |
| (V) | 24146 | 4-[4-(1H-imidazol-1-yl)-2-thienyl]-3-methyl-4-oxobutyric acid | C12H12N2O3S | 详情 | 详情 |
Extended Information