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【结 构 式】 
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【分子编号】69157 【品名】2-methyl-4-quinazolinone;2-Methyl-4-quinazolone;2-Methylquinazolone;3H-2-Methyl-4-oxoquinazoline;4-Hydroxy-2-methylquinazoline;2-Methyl-4-oxoquinazoline;2-Methyl-4(3H)-quinazolone;2-Methyl-4(3H)-quinazolinone;2-Methyl-3H-quinazolin-4-one 【CA登记号】1769-24-0 |
【 分 子 式 】C9H8N2O 【 分 子 量 】160.1754 【元素组成】C 67.49% H 5.03% N 17.49% O 9.99% |
合成路线1
该中间体在本合成路线中的序号：(II)Amination and cyclization of methyl 2-aminobenzoate (I) with acetonitrile in the presence of HCl at reflux gives 2-methyl-4-quinazolinone (II), which by chlorination by means of POCl3 in the presence of DIEA in refluxing toluene or in the absence at 120 °C yields 4-chloro-2-methylquinazoline (III). Finally, intermediate (III) is condensed with N-(4-methoxyphenyl)-N-methylamine (IV) in the presence of HCl in isopropanol .
| 【1】 Sirisoma, N., Pervin, A., Zhang, H. et al. Discovery of N-(4-methoxyphenyl)-N,2- dimethylquinazolin-4-amine, a potent apoptosis induced and efficacious anticancer agent with high blood brain barrier penetration. J Med Chem 2009, 52(8): 2341-51. |
| 【2】 Jaing, S., Cai, S.X., Pervin, A. et al. (Myrexis, Inc.; EpiCept Corp.). Compounds and therapeutical uses thereof. EP 1660092, JP 2007524637, US 2005137213, US 7618975, WO 2005003100. |
| 【3】 Cai, S.X., Anderson, M.B., Willardsen, A., Sirisoma, N.S., Zhang, H.,Suzuki, K. (Myriad Genetics, Inc.; EpiCept Corp.). Nitrogen containing bicyclic compounds and therapeutic use thereof EP 1833482, WO 2006074147. |
| 【4】 Anderson, M.B., Willardsen, J.A., Weiner, W.S. et al. (Myrexis, Inc.). Compounds and therapeutical uses thereof. US 2010069383. |
| 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) | 11161 | methyl 2-aminobenzoate; Methyl anthranilate | 134-20-3 | C8H9NO2 | 详情 | 详情 |
| (II) | 69157 | 2-methyl-4-quinazolinone;2-Methyl-4-quinazolone;2-Methylquinazolone;3H-2-Methyl-4-oxoquinazoline;4-Hydroxy-2-methylquinazoline;2-Methyl-4-oxoquinazoline;2-Methyl-4(3H)-quinazolone;2-Methyl-4(3H)-quinazolinone;2-Methyl-3H-quinazolin-4-one | 1769-24-0 | C9H8N2O | 详情 | 详情 |
| (III) | 69158 | 4-chloro-2-methylquinazoline | 6484-24-8 | C9H7ClN2 | 详情 | 详情 |
| (IV) | 69159 | 4-methoxy-N-methylaniline hydrochloride | C8H11NO.HCl | 详情 | 详情 |