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【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%

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:(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
Extended Information