|
【结 构 式】 
|
【分子编号】28942 【品名】methyl (E)-3-[6-(methylsulfanyl)-4-oxo-3(4H)-quinazolinyl]-2-propenoate 【CA登记号】 |
【 分 子 式 】C13H12N2O3S 【 分 子 量 】276.31596 【元素组成】C 56.51% H 4.38% N 10.14% O 17.37% S 11.6% |
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 cyclization of methyl-5-(methylthio)anthranilate (I) with formamide (II) by heating at 190 C gives 6-(methylthio)-4(3H)-quinazolinone (III), which is condensed with methyl 3-chloroacrylate (IV) by means of NaH yielding methyl 3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoate (V). Finally, this compound is hydrolyzed with refluxing 6N HCl. The same procedure of synthesis can also be performed from 5-(methylthio)anthranilic acid instead of methyl 5-(methylthio)anthranilate (I).
| 【1】 LeMahieu, R.A.; et al.; (E)-3-(4-Oxo-4H-quinazolin-3-yl=-2-propenoic acids, a new series of antiallergy agents. J Med Chem 1983, 26, 3, 420-423. |
| 【2】 Lemahieu, R.A.; Nason, W.C. (Hoffmann-La Roche, Inc.); Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives. EP 0023594; JP 8125167; US 4281127 . |
| 【3】 Serradell, M.N.; Castaner, J.; Chu, S.S.; Tiacrilast. Drugs Fut 1985, 10, 2, 131. |
| 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) | 28939 | methyl 2-amino-5-(methylsulfanyl)benzoate | C9H11NO2S | 详情 | 详情 | |
| (II) | 16598 | Formamide | 75-12-7 | CH3NO | 详情 | 详情 |
| (III) | 28940 | 6-(methylsulfanyl)-4(3H)-quinazolinone | C9H8N2OS | 详情 | 详情 | |
| (IV) | 28941 | methyl (E)-3-chloro-2-propenoate | C4H5ClO2 | 详情 | 详情 | |
| (V) | 28942 | methyl (E)-3-[6-(methylsulfanyl)-4-oxo-3(4H)-quinazolinyl]-2-propenoate | C13H12N2O3S | 详情 | 详情 |
Extended Information