3920-83-0

Usage

Uses

Used in Organic Synthesis:
N-Amino-3-methylindole is used as a building block in organic synthesis for the creation of complex molecular structures. Its unique chemical properties allow it to participate in a variety of reactions, making it a valuable component in the synthesis of new compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, N-Amino-3-methylindole is utilized as a key intermediate in the development of new drugs and therapeutic compounds. Its versatility in chemical reactions contributes to the exploration of novel drug candidates with potential therapeutic benefits.
Used in Drug Discovery and Development:
N-Amino-3-methylindole plays a significant role in drug discovery and development, as its unique properties enable the design and synthesis of innovative pharmaceutical agents. N-Amino-3-methylindole's potential applications in this field have attracted considerable attention from researchers and pharmaceutical companies alike, as it may lead to the creation of new treatments for various diseases and conditions.

Upstream product

• 83-34-1 3-Methylindole 
• 2950-43-8 hydroxylamine-O-sulfonic acid 

Downstream Products

• 866461-72-5 1-[N-methyl-2'-(phenylsulfanyl)acetamido]-3-methylindole 

Relevant academic research and scientific papers

N-amination of indoles on pilot-plant scale via simultaneous and proportional metering of reagents

The N-amination of indoles on large scale, utilizing a portable Coriolis mass flow metering and pumping system that provides precise dispensing of two reagent streams simultaneously and proportionally, is described.

PROCESS FOR THE PREPARATION OF N-AMINO SUBSTITUTED HETEROCYCLIC COMPOUNDS

An improved process for the preparation of N-amino nitrogen heterocyclic compounds is disclosed and claimed. In an ambodiment of this invention, a compound of the formula (VI) is prepared starting from the corresponding indole derivative by way of N-amination and subsequently forming an hydrazone by the reaction with a keto compound in a single step. Further reduction of the hydrazone and subsequent coupling with a pyridine compound affords the compound of formula VI or a suitable salt thereof.

Synthesis and structure-activity relationships of N-propyl-N-(4- pyridinyl)-1H-indol-1-amine (besipirdine) and related analogs as potential therapeutic agents for Alzheimer's disease

A series of novel N-(4-pyridinyl)-1H-indol-1-amines and other heteroaryl analogs was synthesized and evaluated in tests to determine potential utility for the treatment of Alzheimer's disease. From these compounds, N-propyl-N- (4-pyridinyl)-1H-indol-1-amine (besipirdine, 4c) was selected for clinical development based on in-depth biological evaluation. In addition to cholinomimetic properties based initially on in vitro inhibition of [3H]quinuclidinyl benzilate binding, in vivo reversal of scopolamine- induced behavioral deficits, and subsequently on other results, 4c also displayed enhancement of adrenergic mechanisms as evidenced in vitro by inhibition of [3H]clonidine binding and synaptosomal biogenic amine uptake, and in vivo by reversal of tetrabenazine-induced ptosis. The synthesis, structure-activity relationships for this series, and the biological profile of 4c are reported.

N-substituted-4-pyrimidinamines and pyrimidinediamines

This invention relates to N-heteroaryl-4-pyrimidinamines of the formula STR1 where R1 is hydrogen, loweralkyl, aryl, or arylloweralkyl; R2 and R3 are independently hydrogen or loweralkyl, or R2 and R3 taken together are aryl; R4 and R5 are independently hydrogen or lowealkyl, or R4 and R5 taken together are aryl; X is hydrogen, halogen, cyano, nitro, amino, loweralkyl, loweralkoxy, trifluoromethyl or STR2 where Y is hydrogen, halogen or loweralkyl; m is an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometrical and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as memory enhancing agents and as analgesic agents.

N-heteroaryl-purin-6-amines useful as analgesic and anticonvulsant agents

This invention relates to a N-heteroaryl-purin-6-amine of the formula STR1 where R1 is hydrogen, lower alkyl, and arylloweralkyl; R2 and R3 are independently hydrogen, lower alkyl or R2 and R3 taken together are aryl; R4 and R5 are independently hydrogen, lower alkyl, or R4 and R5 taken together are aryl; R6 is hydrogen, lower alkyl, aryl, arylloweralkyl, STR2 where R2, R3, R4 and R5 are as defined above, and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometric and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as analgesic and anticonvulsant agents.

Aminations with O-Diphenylphosphinylhydroxylamine. A Critical Evaluation

A critical evaluation is presented of the scope of amination reactions with O-diphenylphosphinylhydroxylamine (ODPH) as compared to those using hydroxylamine-O-sulfonic acid (HOSA).Aminations with ODPH of isopropyl, t-butyl and cyclohexyl carbanions derived from the corresponding Grignard reagents, gave the corresponding amines in 36, 34 and 50 percent yields, respectively.The amination with HOSA of the same carbanions under similar conditions was unsuccessful.The aminative quaternization of the tertiary nitrogen of pyridine and quinoline with ODPH proceeded with comparable yields to those obtained with HOSA.An improved one flask amination with ODPH of indole, skatole and carbazole was achieved in 52 - 62 percent yields.The amination under the same conditions using HOSA gave consistently lower yields.Several other amination reactions which have been reported for HOSA were unsuccessful using ODPH.The conclusion is reached that overall the ODPH reagent is much less versatile than HOSA.Nevertheless, in the aminations of NH groups of heterocyclic compounds ODPH appears to be superior to HOSA and is the reagent of choice, in particular, since the preparation of ODPH is much less harzardous than that of HOSA. - Keywords: Synthesis, O-Diphenylphosphinylhydroxylamine, Hydroxylamine-O-sulfonic Acid, N-Amino Derivatives, N-Amino Heterocyclic Compounds