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【结 构 式】 
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【分子编号】19448 【品名】[3-(2-aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide 【CA登记号】 |
【 分 子 式 】C13H19N3 【 分 子 量 】217.31408 【元素组成】C 71.85% H 8.81% N 19.34% |
合成路线1
该中间体在本合成路线中的序号：(XVII)4) The condensation of hydrazine (II) with 3-nitropropanal (XIV) in water gives the nitrobutylidenehydrazino derivative (XV), which is cyclized with PPE as before yielding N-methyl-3-(2-nitroethyl)-1H-indole-5-methansulfonamide (XVI), which is reduced with H2 over Pd/C in ethyl acetate to afford the 2-aminoethyl compound (XVII). Finally, this compound is methylated with ICH3 and NaHCO3 or with formaldehyde and NaBH4
| 【1】 Oxford, A.W. (Glaxo Group Ltd.); An indole derivative.. GB 2162522 . |
| 【2】 Coates, I.H.; Dowle, M.D. (Glaxo Group Ltd.); Heterocyclic compounds.. FR 2530625; GB 2124210; US 4816470 . |
| 【3】 Humphrey, P.P.A.; Feniuk, W.; Perren, M.J.; Oxford, A.W.; Brittain, R.T.; Prous, J.; Castaner, J.; SUMATRIPTAN SUCCINATE < Prop INNM; BAN >. Drugs Fut 1989, 14, 1, 35. |
| 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) | 19432 | (4-aminophenyl)-N-methylmethanesulfonamide; 4-amino-N-ethylbenzylmethanesulfamide | 109903-35-7 | C8H12N2O2S | 详情 | 详情 |
| (II) | 19433 | (4-hydrazinophenyl)-N-methylmethanesulfonamide | 88933-16-8 | C8H13N3O2S | 详情 | 详情 |
| (XIV) | 19445 | 4-nitrobutanal | C4H7NO3 | 详情 | 详情 | |
| (XV) | 19446 | N-methyl(4-[[(E)-5-nitro-1-pentenyl]amino]phenyl)methanesulfonamide | C13H19N3O4S | 详情 | 详情 | |
| (XVI) | 19447 | N-methyl[3-(2-nitroethyl)-1H-indol-5-yl]methanesulfonamide | C12H15N3O4S | 详情 | 详情 | |
| (XVII) | 19448 | [3-(2-aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide | C13H19N3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XVII)5) The condensation of hydrazino compound (II) with 4,4-dimethoxybutyronitrile (XVIII) gives the cyanobutylideneamino derivative (XIX), which is cyclized with PPE as before yielding 3-(cyanomethyl)-N-methyl-1H-indole-5-methanesulfonamide (XX). Finally, this compound is reduced with H2 over Rh/Al2O3 to afford the 2-aminoethyl derivative (XVII), already obtained.
| 【1】 Oxford, A.W. (Glaxo Group Ltd.); An indole derivative.. GB 2162522 . |
| 【2】 Coates, I.H.; Dowle, M.D. (Glaxo Group Ltd.); Heterocyclic compounds.. FR 2530625; GB 2124210; US 4816470 . |
| 【3】 Humphrey, P.P.A.; Feniuk, W.; Perren, M.J.; Oxford, A.W.; Brittain, R.T.; Prous, J.; Castaner, J.; SUMATRIPTAN SUCCINATE < Prop INNM; BAN >. Drugs Fut 1989, 14, 1, 35. |
| 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) | 19432 | (4-aminophenyl)-N-methylmethanesulfonamide; 4-amino-N-ethylbenzylmethanesulfamide | 109903-35-7 | C8H12N2O2S | 详情 | 详情 |
| (II) | 19433 | (4-hydrazinophenyl)-N-methylmethanesulfonamide | 88933-16-8 | C8H13N3O2S | 详情 | 详情 |
| (XVII) | 19448 | [3-(2-aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide | C13H19N3 | 详情 | 详情 | |
| (XVIII) | 15350 | 4,4-diethoxybutanenitrile; 4,4-diethoxy-butanenitrile | 18381-45-8 | C8H15NO2 | 详情 | 详情 |
| (XIX) | 19450 | (4-[2-[(E)-3-cyanopropylidene]hydrazino]phenyl)-N-methylmethanesulfonamide | C12H16N4O2S | 详情 | 详情 | |
| (XX) | 19451 | [3-(cyanomethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide | C12H13N3O2S | 详情 | 详情 |