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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 2 条

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
Extended Information