147009-33-4

Basic information

• Product Name: rac-6-Cyano-3-N-methylamino-1,2,3,4-tetrahydrocarbazole
• Synonyms: rac-6-Cyano-3-N-methylamino-1,2,3,4-tetrahydrocarbazole;2,3,4,9-Tetrahydro-3-(MethylaMino)-1H-carbazole-6-carbonitrile;3-(MethylaMino)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile;6-Cyano-3-N-methylamino-1,2,3,4-tetrahydrocarbazole
• CAS NO: 147009-33-4
• Molecular Formula: C14H14N3
• Molecular Weight: 224.28106
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 147009-33-4.mol

Chemical Properties

• Boiling Point: 437.469 °C at 760 mmHg
• Flash Point: 218.374 °C
• Appearance: /
• Density: 1.221 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: rac-6-Cyano-3-N-methylamino-1,2,3,4-tetrahydrocarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: rac-6-Cyano-3-N-methylamino-1,2,3,4-tetrahydrocarbazole(147009-33-4)
• EPA Substance Registry System: rac-6-Cyano-3-N-methylamino-1,2,3,4-tetrahydrocarbazole(147009-33-4)

Safety Data

• Hazardous Substances Data: 147009-33-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Intermediate in the preparation of Frovatriptan

InChI:InChI=1/C14H15N3/c1-16-10-3-5-14-12(7-10)11-6-9(8-15)2-4-13(11)17-14/h2,4,6,10,16-17H,3,5,7H2,1H3

Downstream Products

• 1233390-20-9 (+)-6-cyano-3-(N-methylamino)-1,2,3,4-tetrahydrocarbazole hydrochloride 

Relevant articles and documents

Process for the production of R-(+)-6-carboxamido-3-N-methylamino-1,2,3,4-tetrahydrocarbazole

The present invention relates to a novel process for the preparation of R-(+)-6-carboxamido-3-N-methylamino-1,2,3,4-tetrahydrocarbazole. The process comprises resolving an enantiomeric mixture of a compound of formula (I):

Medicaments 1,2,3,4-tetrahydrocarbazoles and 5-HT1 agonist use thereof

Use of a compound of general formula (I): STR1 wherein R1 represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C1-6 alkyl, C1-6 alkoxy, arylC1-6 alkoxy, --CO2 R4, --(CH2)n CN, --(CH2)n CONR5 R6, --(CH2)n SO2 NR5 R6, C1-6 alkanoylamino(CH2)n, or C1-6 alkylsulphonylamino(CH2)n ; R4 represents hydrogen, C1-6 alkyl or arylC1-6 alkyl; R5 and R6 each independently represent hydrogen or C1-6 alkyl, or R5 and R6 together with the nitrogen atom to which they are attached form a ring; n represents 0, 1 or 2; and R2 and R3 each independently represent hydrogen, C1-6 alkyl or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring; or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of a condition where a 5-HT1 -like agonist is indicated, for example migraine. Novel compounds of formula (I), processes for preparing them and pharmaceutical compositions containing them are also described.

PROCESS FOR PREPARING AN ENANTIOMER OF A CARBAZOLE DERIVATIVE

A (+) or (-) enantiomer of a compound of formula (I) wherein R. sup.4 is methyl or ethyl, or a salt, solvate or hydrate thereof, processes for preparing said compounds and pharmaceutical compositions containing them. Compounds of formula (+) are 5-HT 1-li

ENANTIOMERS OF CARBAZOLE DERIVATIVES AS 5-HT1-LIKE AGONISTS

A (+)or (-) enantiomer of a compound of formula (I) wherein R. sup.4 is methyl or ethyl, or a salt, solvate or hydrate thereof, processes for preparing said compounds and pharmaceutical compositions containing them. Compounds of formula (+) are 5-HT 1-lik

Tetrahydrocarbazole derivatives for the manufacture of a medicament for the treatment of a disease where a 5-HT1-like agonist is indicated

Use of a compound of general formula (I): wherein : R1represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C1 6alkyl, C1 6alkoxy, arylC1 6alkoxy, -CO2R4, -(CH2)nCN, -(CH2)nCONR5R6,-(CH2)nSO2NR5R6,C1 6alkanoylamino(CH2)n, or C1 6alkylsulphonylamino (CH2)n; R4represents hydrogen, C1 6alkyl or arylC1 6alkyl; R5 and R6each independently represent hydrogen or C1 6alkyl, or R5 and R6 together with the nitrogen atom to which they are attached form a ring; nrepresents 0, 1 or 2; and R2 and R3each independently represent hydrogen, C1 6alkyl or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring; or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of a condition where a 5-HT1-like agonist is indicated, for example migraine. Novel compounds of formula (I), processes for preparing them and pharmaceutical compositions containing them are also described.