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【结 构 式】 
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【分子编号】30357 【品名】4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbohydrazide 【CA登记号】 |
【 分 子 式 】C17H22N4O 【 分 子 量 】298.38804 【元素组成】C 68.43% H 7.43% N 18.78% O 5.36% |
合成路线1
该中间体在本合成路线中的序号：(III)The hydrogenation of 1-methyl-7,8-lysergic acid ethyl ester (I) with H2 over PtO2 gives 1-methyl-9,10-dihydroisolysergic acid methyl ester (II), which by reaction with hydrazine is converted into the corresponding hydrazide (III). The reaction of (III) with NaNO2-HCl yields the expected azide (IV), which is submitted to a Curtius degradation by heating and hydrolysis to afford 1,6-dimethyl-8(alpha)-aminoergoline (V). Finally, this compound is treated with N,N-dimethylsulfamoyl chloride (VI) and 2,6-lutidine in methylene chloride.
| 【1】 Stuetz, P.; Fehr, T.; Stadler, P. (Novartis AG); Sulfonamido and sulfamoylamino-ergoline-I derivatives. BE 0849745; CA 1092100; CH 620441; DE 2656344; ES 454442; FR 2336135; GB 1567484; JP 7778900; NL 7614018 . |
| 【2】 Serradell, M.N.; Koch, H.; Castaner, J.; Mesulergine Hydrochloride. Drugs Fut 1984, 9, 3, 191. |
| 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) | 30355 | methyl 4,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylate | C18H20N2O2 | 详情 | 详情 | |
| (II) | 30356 | methyl 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate | C18H22N2O2 | 详情 | 详情 | |
| (III) | 30357 | 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbohydrazide | C17H22N4O | 详情 | 详情 | |
| (IV) | 30358 | 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbonyl azide | C17H19N5O | 详情 | 详情 | |
| (V) | 30359 | 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-ylamine; 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-amine | C16H21N3 | 详情 | 详情 | |
| (VI) | 30360 | [(Chlorosulfonyl)(methyl)amino]methane;dimethylsulfamoyl chloride | 13360-57-1 | C2H6ClNO2S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)By reductocondensation of amino (IV) with 6,6-dimethylhept-2-en-4-ynal (VI) by means of NaBH4 in methanol.
| 【1】 Stutz, A. (Novartis AG); Propenylamines, pharmaceutical compositions containing them and their use as pharmaceuticals. EP 0024587; JP 56032440; JP 63313753; Us 4755534 . |
| 【2】 Serradell, M.N.; Castaner, J.; SF-86327. Drugs Fut 1984, 9, 6, 425. |