661489-23-2

Usage

Uses

Used in Pharmaceutical Industry:
(E)-3-(4-Amino-3,5-dimethylphenyl)acrylonitrile Hydrochloride is used as a key intermediate in the synthesis of 5,6-substituted pyrimidines, which are important for the development of new antiviral drugs. Specifically, these pyrimidines have the potential to inhibit HIV strains that are resistant to reverse transcriptase inhibitors, offering a promising avenue for the treatment of drug-resistant HIV infections.

InChI:InChI=1S/C11H12N2.ClH/c1-8-6-10(4-3-5-12)7-9(2)11(8)13;/h3-4,6-7H,13H2,1-2H3;1H/b4-3+;

Upstream product

• 4102-53-8 4-iodo-2,6-dimethylaniline 
• 107-13-1 acrylonitrile 
• 500292-86-4 3-(4-amino-3,5-dimethylphenyl)acrylonitrile 
• 114886-15-6 N'-(4-bromo-2,6-dimethylphenyl)-N,N-dimethylmethanimidamide 
• 86955-76-2 N-(benzyloxycarbonyl)-2,6-dimethyl-4-nitroaniline 
• 16947-63-0 2,6-dimethyl-4-nitroaniline 
• 87-62-7 2,6-dimethylaniline 

Relevant academic research and scientific papers

Rilpivirine midbody preparing technology

The invention belongs to the field of medicinal chemistry, and particularly relates to a rilpivirine midbody preparing technology. The technology comprises the steps that 1, 4-bromo-2,6-dimethylaniline and acrylonitrile react under the catalysis of pallad

Pharmaceutical compositions comprising a basic drug compound, a surfactant, and a physiologically tolerable water soluble acid

The invention provides a novel pharmaceutical composition comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base characterized in that the acid respectively base:drug compound ratio is at least 1:1 by weight.

PROCESS FOR RILPIVIRINE

The present invention provides a novel process for the preparation of 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile. The present invention also provides a novel process for the preparation of 4-iodo-2,6-dimethyl benzenamine. The present invention further provides an improved process for the preparation of rilpivirine. The present invention further provides a tosylate salt of rilpivirine, process for its preparation and pharmaceutical compositions comprising it.

RILPIVIRINE PROCESS

Disclosed is process for the preparation of a key Rilpivirine intermediate namely, (E)-4-(2-cyanoethenyl)-2,6-dimethylphenylamine hydrochloride (II) by a process comprising reaction of the tetrafluoroborate salt of the diazonium ion of 2,6-dimethyl-4-amin

RILPIVIRINE HYDROCHLORIDE

The present invention provides a novel process for the preparation of rilpivirine. The present invention also provides a novel process for the preparation of rilpivirine hydrochloride. The present invention further provides a rilpivirine hydrochloride monohydrate, process for its preparation and pharmaceutical compositions comprising it.

RILPIVIRINE HYDROCHLORIDE

As used herein the term "room temperature" refers to a temperature of about 25°C to about 35°C. According to one aspect of the present invention, there IS provided a novel process for the preparation of rilpivirine, which comprises: a) condensing the (E)-3-( 4-amino-3,5-dimethylphenyl)acrylonitrile hydrochloride with 4-( 4-chloropyrimidin-2-ylamino )benzonitrile m the presence of Nmethylpyrrolidone; b) heating the contents obtained in step (a) at about 75 to 95°C to obtain a solution; c) cooling the solution obtained in step (b) at below 35°C; d) adding water to the reaction mass; and e) isolating rilpivirine. The reaction in step (b) may preferably be heated to 100 to 110°C. Step (c) may preferably be carried out at room temperature. Rilpivirine may be isolated in step (e) by the methods known such as Filtration or centrifugation.

PROCESS FOR RILPIVIRINE

The present invention provides a novel process for the preparation of 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile. The present invention also provides a novel process for the preparation of 4-iodo-2,6-dimethyl benzenamine. The present invention further provides an improved process for the preparation of rilpivirine. The present invention further provides a tosylate salt of rilpivirine, process for its preparation and pharmaceutical compositions comprising it.

Ligandless Heck coupling between a halogenated aniline and acrylonitrile catalyzed by Pd/C: Development and optimization of an industrial-scale Heck process for the production of a pharmaceutical intermediate

The aniline derivative 3 is a key building block of rilpivirine (TMC278) 2, a new potent NNRTI compound under clinical evaluation. In this paper we describe the development of a new synthesis of 3 based on a Heck coupling between a halogenated aniline and acrylonitrile using low loading of Pd/C (0.5 mol %) as catalyst. This resulted in a process which has been successfully transferred into production on 2400 mol-scale (6000 L reactor)

PROCESSES FOR THE PREPARATION OF 4-[[4-[[4-(2-CYANOETHENYL)-2,6-DIMETHYLPHENYL]AMINO]-2-PYRIMIDINYL]AMINO]BENZONITRILE

Processes for the preparation of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile of formula (I), a N-oxide, a pharmaceutically acceptable acid addition salt, a quaternary amine or a stereochemically isomeric form thereof are provided, said processes comprise a) reacting 4-(2-cyanoethenyl)-2,6-dimethylbenzenamine with an intermediate of formula (III) in the presence of a suitable solvent; b) reacting an intermediate of formula (IV) with acrylonitrile in the presence of a suitable palladium catalyst, a suitable base and a suitable solvent; c) dehydrating the corresponding amide of the compound of formula (I).