98623-50-8

Usage

Uses

Used in Pharmaceutical Industry:
N-Methyl-1H-Indole-5-EthaneSulphonamide is used as a key reagent in the synthesis of Naratriptan Hydrochloride (N378730), a triptan drug specifically designed for the treatment of migraine headaches. Triptans are known for their ability to alleviate migraine symptoms by constricting blood vessels and reducing inflammation. As a reagent, N-Methyl-1H-Indole-5-EthaneSulphonamide contributes to the production of this effective medication, helping to improve the quality of life for those who suffer from migraines.

InChI:InChI=1/C11H14N2O2S/c1-12-16(14,15)7-5-9-2-3-11-10(8-9)4-6-13-11/h2-4,6,8,12-13H,5,7H2,1H3

Upstream product

• 53654-36-7 3-vinyl-1H-indole 
• 157835-85-3 1,1-dimethylethyl 3-ethenyl-1H-indole-1-carboxylate 
• 1200070-42-3 2-(4-amino-3-iodo-phenyl)ethanesulfonic acid methylamide 
• 1268265-99-1 N-[2-ethynyl-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide 
• 1268265-95-7 N-[4-(2-{methylsulfamoyl}ethyl)-2-{2-(trimethylsilanyl)ethynyl}phenyl]acetamide 
• 1268265-90-2 N-[2-iodo-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide 
• 98623-16-6 2-(4-amino-phenyl)ethanesulfonic acid methylamide 
• 1204192-94-8 2-(3-phenylsulfanyl-1H-indol-5-yl)ethanesulfonicacid methylamide 
• 1305334-90-0 2-(1H-indol-5-yl)-N-methyl ethenesulfonamide 
• 1190200-23-7 phenyl 2-(1H-indol-5-yl)ethanesulfonate 
• 74-89-5 methylamine 
• 1025797-51-6 5-[2-(methylsulfamoyl)ethyl]-1H-indole-2-carboxylic acid 

Downstream Products

• 121679-20-7 N-methyl-2-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide 
• 143388-64-1 naratriptan hydrochloride 
• 121679-13-8 naratriptan 

Relevant academic research and scientific papers

The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan

The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the synthesis of the anti-migraine drug naratriptan and it also can be used for the late-stage functionalization of natural products or medicines.

An efficient synthetic protocol for the synthesis of 2-(1H-Indol-5-yl)-ethanesulfonic acid methylamide: A potential synthetic precursor for naratriptan and its novel 3-substituted derivatives

Background: The 3-Substituted indoles are found to possess a wide range of biological and pharmacological activities. The efficient and impurity free scalable preparation of 2-(1H-Indol-5-yl)-ethanesulfonic acid methylamide has been successfully achieved

A PROCESS FOR THE SYNTHESIS OF NARATRIPTAN

The present invention relates to a process for preparing naratriptan or a salt thereof, the process comprising: (a) reacting a compound of formula (3) with a compound of the formula HCCR wherein Z is a protecting group, Y is a leaving group and R is a trialkyl silyl group, a trialkylstannyl group or a zinc (II) halide, to obtain the compound of formula (4); (b) converting the compound of formula (4) to a compound of formula (5) wherein Z'' is hydrogen or a benzyl group; (c) converting the compound of formula (5) to naratriptan; and (d) optionally converting naratriptan to a salt thereof. The present invention also provides novel compounds (3) and (4) and processes for their preparation.

PROCESS FOR PREPARING INDOLE DERIVATIVES

The present invention provides a process for the preparation of indole derivatives, specifically N- methyl-1H-indole-5-ethanesulfonamide of formula (I), involving novel intermediate, which is used as key intermediate for the synthesis of naratriptan of formula (II), and its pharmaceutically acceptable salts thereof high yield and purity.

PROCESS FOR PREPARATION OF NARATRIPTAN HYDROCHLORIDE

The present invention relates to an improved process for the preparation of N-methyl-3- (1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride of formula (I) having less than 0.15 % area by HPLC of 3-(1-methyl-4-piperidinyl)-1H-indole-5- ethanesulfonamide (1A) and intermediates thereof.

PROCESS FOR THE PREPARATION OF INDOLE DERIVATIVES

The present invention relates to a novel process for the preparation of indole derivatives. In particular, present invention relates to the process for preparing naratriptan of formula (I), and its salts using novel intermediates. The present invention also relates to novel synthetic intermediates useful in the preparation of naratriptan hydrochloride.

5-substituted-3-aminoalkyl indole derivatives for migraine

Indole derivatives are disclosed of the general formula (I): STR1 wherein R1 is hydrogen, C1-6 alkyl or C3-6 alkenyl; R2 is a hydrogen, C1-3 alkyl, C3-6 alkenyl, phenyl, phen(C1-4)alkyl or C5-7 cycloalkyl; R3 and R4 are hydrogen, C1-3 alkyl or propenyl groups or together form an aralkylidene group; Alk is C2 -C3 alkylene chain and A is C2 -C5 alkylene chain and its physiologically acceptable salts and solvates. The compounds may be prepared, for example, by cyclization of a compound of general formula (II): STR2 where Q is the group NR3 R4 or a protected derivative thereof or a leaving group and R1 l, R2, R3, R4, A and Alk are as defined for formula (I). The compounds have a selective vosoconstrictor action and are useful in treating pain such as migraine. The compounds may be formulated as pharmaceutical compositions in conventional manner, preferably for oral administration.