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【结 构 式】 
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【分子编号】34621 【品名】4,5-dimethoxy-1,2-benzenediamine; 2-amino-4,5-dimethoxyphenylamine 【CA登记号】 |
【 分 子 式 】C8H12N2O2 【 分 子 量 】168.19556 【元素组成】C 57.13% H 7.19% N 16.66% O 19.02% |
合成路线1
该中间体在本合成路线中的序号：(III)Treatment of veratrole (I) with aqueous HNO3 and H2SO4 yields 1,2-dinitrobenzene derivative (II), which is then converted into diamine (III) by hydrogenation over Pd/C in HOAc/EtOH or over PtO2. Finally, reaction of diamine (III) with phenyl glyoxal (IV) in EtOH and HOAc or HCl affords the desired product.
| 【1】 Bohmer, F.D.; Chen, J.; Gazit, A.; McMahon, G.; Levitzki, A.; App, H.; Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: Structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins. J Med Chem 1996, 39, 11, 2170. |
| 【2】 Treatment of platelet derived growth factor related disorders such as cancers using inhibitors of platelet derived growth receptor. EP 1000617; US 5700823; WO 9519169 . |
| 【3】 Levitzki, A.; Hirth, K.P.; Schwartz, D.P.; Tang, P.C.; Ullrich, A.; Haimichael, J.; Shawver, L.K.; Szekely, I.; Mann, E.; Orfi, L.; Slamon, D.; Keri, G.; Kabbinavar, F.F.; Gazit, A.; Bajor, T.; Lammers, R. (Sugen, Inc.); Treatment of platelet derived growth factor related disorders such as cancers. US 5990141 . |
| 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) | 17398 | 2-methoxyphenyl methyl ether; Veratrole; 1,2-dimethoxybenzene | 91-16-7 | C8H10O2 | 详情 | 详情 |
| (II) | 43039 | 2-methoxy-4,5-dinitrophenyl methyl ether; 1,2-dimethoxy-4,5-dinitrobenzene | 3395-03-7 | C8H8N2O6 | 详情 | 详情 |
| (III) | 34621 | 4,5-dimethoxy-1,2-benzenediamine; 2-amino-4,5-dimethoxyphenylamine | C8H12N2O2 | 详情 | 详情 | |
| (IV) | 43040 | 2-oxo-2-phenylacetaldehyde | C8H6O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)Oxidation of 3-acetylthiophene (I) with selenium dioxide in refluxing dioxan provided 3-thienylglyoxaldehyde hydrate (II). This was then condensed with 4,5-dimethoxy-1,2-phenylenediamine (III) in boiling EtOH to produce the target quinoxaline, which was finally isolated as the hydrochloride salt.
| 【1】 Myers, M.R.; Maguirre, M.P.; Spada, A.P.; Persons, P.E. (Aventis Pharmaceuticals, Inc.); Bis mono- and bicyclic aryl and heteroaryl cpds. which inhibit EGF and/or PDGF receptor tyrosine kinase. US 5480883 . |