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【结 构 式】 
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【分子编号】40430 【品名】(6aR,9R,10aR)-5-chloro-7-methyl-9-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline 【CA登记号】 |
【 分 子 式 】C19H25ClN2OS 【 分 子 量 】364.93908 【元素组成】C 62.53% H 6.9% Cl 9.71% N 7.68% O 4.38% S 8.79% |
合成路线1
该中间体在本合成路线中的序号：(III)It is prepared in two different ways, both starting from 6-methyl-8-methanesulfonyloxymethylergolin (II), m.p. 192-4 C, prepared by reaction of the corresponding hydroxy compound (I) with methanesulfonyl chloride in pyridine: 1) The starting product (II) is first chlorinated with N-chlorosuccinimide (A) in dioxane to 2-chloro-6-methyl-8-methanesulfonyloxymethylergolin (III), which is then treated with sodium cyanide in DMSO. 2) The starting product (II) is first treated with sodium cyanide in DMSO to give 6-methyl-8-cyanomethylergolin (IV), which is then chlorinated with N-chlorosuccinimide (A) in dioxane.
| 【1】 Castañer, J.; Chatterjee, S.S.; Lergotrile. Drugs Fut 1976, 1, 2, 63. |
| 【2】 Clemens, J.A.; et al. (Eli Lilly and Company); D-6-methyl-2,8-disubstituted ergolines. DE 2335750; ES 446789; FR 2193606; GB 1423065; JP 57081487 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 40429 | Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione | 128-09-6 | C4H4ClNO2 | 详情 | 详情 |
| (I) | 10051 | [(6aR,9R,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methanol; 9,10-Dyhydrosergol | 18051-16-6 | C16H20N2O | 详情 | 详情 |
| (II) | 40428 | (6aR,9R,10aR)-7-methyl-9-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline | C19H26N2OS | 详情 | 详情 | |
| (III) | 40430 | (6aR,9R,10aR)-5-chloro-7-methyl-9-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline | C19H25ClN2OS | 详情 | 详情 | |
| (IV) | 40431 | 2-[(6aR,9S,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]acetonitrile | C17H19N3 | 详情 | 详情 |