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【结 构 式】 
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【药物名称】REV-3164, RHC-3164 【化学名称】7-Chloro-5-propyl[1,2,4]triazolo[4,3-a]quinoxaline-1,4(2H,5H)-dione 【CA登记号】80708-33-4 【 分 子 式 】C12H11ClN4O2 【 分 子 量 】278.70007 |
【开发单位】Revlon (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS |
合成路线1
The cyctization of 4-chloro-2-(propylamino)aniline (I) with oxalyl chloride (II) in hot o-dichlorobenzene gives 1-propyl-7-chloroquinoxaline-2,3-dione (III), which by reaction with SOCl2 in DMF is converted to 3,7-dichloro-1-propyl-1H-quinoxalin-2-one (IV). The condensation of (IV) with ethyl carbazate (V) in refluxing acetonitrile affords ethyl 3-(7-chloro-1-propyl-2-oxo-1H-quinoxalin-3-yl)carbazate (VI), which is finally cyclized by heating at 260 C.
| 【1】 Brown, R.E.; Georgiev, V.; Kropp, P.; Loev, B. (USV Pharmaceutical Corp.); Triazaloquinoxalin-1,4-diones. EP 0039920; JP 57004988; US 4400382 . |
| 【2】 Chu, S.S.; Castaner, J.; Serradell, M.N.; RHC-3164. Drugs Fut 1985, 10, 12, 985. |
| 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) | 29840 | 4-chloro-N(2)-propyl-1,2-benzenediamine; N-(2-amino-5-chlorophenyl)-N-propylamine | C9H13ClN2 | 详情 | 详情 | |
| (II) | 29841 | Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride | 79-37-8 | C2Cl2O2 | 详情 | 详情 |
| (III) | 29842 | 7-chloro-1-propyl-1,4-dihydro-2,3-quinoxalinedione | C11H11ClN2O2 | 详情 | 详情 | |
| (IV) | 29843 | 3,7-dichloro-1-propyl-2(1H)-quinoxalinone | C11H10Cl2N2O | 详情 | 详情 | |
| (V) | 27366 | Ethyl hydrazinecarboxylate; Ethyl 1-hydrazinecarboxylate | 4114-31-2 | C3H8N2O2 | 详情 | 详情 |
| (VI) | 29844 | ethyl 2-(6-chloro-3-oxo-4-propyl-3,4-dihydro-2-quinoxalinyl)-1-hydrazinecarboxylate | C14H17ClN4O3 | 详情 | 详情 |
Extended Information