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【结 构 式】

【分子编号】19432

【品名】(4-aminophenyl)-N-methylmethanesulfonamide; 4-amino-N-ethylbenzylmethanesulfamide

【CA登记号】109903-35-7

【 分 子 式 】C8H12N2O2S

【 分 子 量 】200.26156

【元素组成】C 47.98% H 6.04% N 13.99% O 15.98% S 16.01%

与该中间体有关的原料药合成路线共 5 条

合成路线1

该中间体在本合成路线中的序号:(I)

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:(I)

2) The condensation of hydrazine (II) with 4,4-dimethoxy-N,N-dimethylbutylamine (VIII) by means of HCl in water gives the butylidenehydrazino compound (IX), which is cyclized with polyphosphate ester (PPE) in CHCl3.

1 Coates, I.H.; Dowle, M.D. (Glaxo Group Ltd.); Heterocyclic compounds.. FR 2530625; GB 2124210; US 4816470 .
2 Oxford, A.W. (Glaxo Group Ltd.); An indole derivative.. GB 2162522 .
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) 19439 4,5-diethoxy-N,N-dimethyl-1-pentanamine; N-(4,5-diethoxypentyl)-N,N-dimethylamine C11H25NO2 详情 详情
(IX) 19440 (4-[2-[(E)-4-(dimethylamino)butylidene]hydrazino]phenyl)-N-methylmethanesulfonamide C14H24N4O2S 详情 详情

合成路线3

该中间体在本合成路线中的序号:(I)

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

合成路线4

该中间体在本合成路线中的序号:(I)

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5

该中间体在本合成路线中的序号:(I)

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