88933-16-8

Usage

Uses

Used in Pharmaceutical Industry:
N-Methyl-4-diazanylsulfabenzamide is used as an intermediate in the synthesis of Sumatriptan, a medication primarily used for the acute treatment of migraine headaches and, less commonly, for the treatment of cluster headaches. Its role in the production process is crucial for creating an effective medication to alleviate the symptoms of these conditions.

InChI:InChI=1/C8H13N3O2S.ClH/c1-10-14(12,13)6-7-2-4-8(11-9)5-3-7;/h2-5,10-11H,6,9H2,1H3;1H

Upstream product

• 109903-35-7 1-(4-aminophenyl)-N-methylmethanesulfonamide 

Downstream Products

• 151140-96-4 avitriptan 

Relevant academic research and scientific papers

Synthesis of n-methyl benzenemethane sulfonamide substituted carbazoles and pyrazoles

Cyclization of 1-(4-hydrazinophenyl)-N-methylmethanesulfonamide hydrochloride (2) with cyclohexanone (3)/N-methyl-4-piperidone (5) afforded the corresponding N-methyl-1-(2,3,4,9-tetrahydro-1H-carbazol-6-yl)methanesulfonamide (4) and N-methyl-1-(2-methyl- 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-8-yl) methane sulfonamide (6). Condensation of compound 2 with substituted aryl β-diketones gave the novel N-methyl-1-[4-(3-methyl-5-phenyl-1H-pyrazol-1- yl)phenyl]methanesulfonamide (8). All the synthesized compounds were characterized by their FT-IR, 1H NMR and mass spectral data.

PREPARATION AND UTILITY OF SUBSTITUTED INDOLES

Disclosed herein are substituted indoles of Formula I, processes of preparation there of, pharmaceutical compositions thereof, and methods of their use there of.

Piperazine, piperidine and tetrahydropyridine derivatives useful as 5-HT1 recepter agonists

A class of N-substituted piperazine, piperadine and tetrahyrdopyridine derivatives of formula (I), further substituted at the 4-position by an optionally substituted aryl-alkyl or heteroaryl-alkyl moiety, are selective agonists of 5-HT1 -like r

An efficient Fischer indole synthesis of avitriptan, a potent 5-HT(1D) receptor agonist

An efficient synthesis of antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaler-aldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5- chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.