【结 构 式】 |
【分子编号】19437 【品名】1H-indol-5-yl-N-methylmethanesulfonamide 【CA登记号】 |
【 分 子 式 】C10H12N2O2S 【 分 子 量 】224.28356 【元素组成】C 53.55% H 5.39% N 12.49% O 14.27% S 14.3% |
合成路线1
该中间体在本合成路线中的序号:(VI)1) The diazotation of 4-amino-N-methylbenzenemethanesulfonamide (I) with NaNO2-HCl followed by reduction with SnCl2 gives the 4-hydrazino compound (II), which is condensed with (phenylthio)acetaldehyde (III) in ethanol yielding the ethylideneamino compound (IV). The cyclization of (IV) with HCl in ethanol affords N-methyl-3-(phenylthio)-1H-indole-5-methansulfonamide (V), which is desulfurized with RaNi in refluxing ethanol-water to give N-methyl-1H-indole-5-methanesulfonamide (VI). The reaction of (VI) with oxalyl chloride and dimethylamine yields the oxalyl derivative (VII), which is finally reduced with LiAlH4 in refluxing THF.
【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 |
(III) | 19434 | 2-(phenylsulfanyl)acetaldehyde | C8H8OS | 详情 | 详情 | |
(IV) | 19435 | N-methyl(4-[2-[(E)-2-(phenylsulfanyl)ethylidene]hydrazino]phenyl)methanesulfonamide | C16H19N3O2S2 | 详情 | 详情 | |
(V) | 19436 | N-methyl[3-(phenylsulfanyl)-1H-indol-5-yl]methanesulfonamide | C16H16N2O2S2 | 详情 | 详情 | |
(VI) | 19437 | 1H-indol-5-yl-N-methylmethanesulfonamide | C10H12N2O2S | 详情 | 详情 | |
(VII) | 19438 | N,N-dimethyl-2-(5-[[(methylamino)sulfonyl]methyl]-1H-indol-3-yl)-2-oxoacetamide | C14H17N3O4S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(VI)3) The condensation of indole (VI) with N,N-diethylchloroacetamide (X) by means of POCl3 gives 3-chloroacetyl-N-methyl-1H-indole-5-methanesulfonamide (XI), which is treated with dimethylamine (XII) in refluxing ethanol to afford the dimethylaminoacetyl derivative (XIII), which is finally reduced with NaBH4 in refluxing propanol.
【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 |
---|---|---|---|---|---|---|
(A) | 19441 | 2-chloro-N,N-diethylacetamide | 2315-36-8 | C6H12ClNO | 详情 | 详情 |
(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 |
(III) | 19434 | 2-(phenylsulfanyl)acetaldehyde | C8H8OS | 详情 | 详情 | |
(IV) | 19435 | N-methyl(4-[2-[(E)-2-(phenylsulfanyl)ethylidene]hydrazino]phenyl)methanesulfonamide | C16H19N3O2S2 | 详情 | 详情 | |
(V) | 19436 | N-methyl[3-(phenylsulfanyl)-1H-indol-5-yl]methanesulfonamide | C16H16N2O2S2 | 详情 | 详情 | |
(VI) | 19437 | 1H-indol-5-yl-N-methylmethanesulfonamide | C10H12N2O2S | 详情 | 详情 | |
(XI) | 19442 | [3-(2-chloroacetyl)-1H-indol-5-yl]-N-methylmethanesulfonamide | C13H15ClN2O | 详情 | 详情 | |
(XII) | 19443 | N-methylmethanamine; N,N-dimethylamine | 124-40-3 | C2H7N | 详情 | 详情 |
(XIII) | 19444 | [3-[2-(dimethylamino)acetyl]-1H-indol-5-yl]-N-methylmethanesulfonamide | C14H19N3O3S | 详情 | 详情 |