500292-94-4

Usage

Uses

Used in Polymer and Plastics Industry:
(E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile is used as a monomer in the production of polymers and plastics due to its ability to form long-chain polymers that are utilized in various applications, including packaging materials and consumer products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, DMMA is used as an intermediate in the synthesis of various drugs. Its unique chemical structure allows for the development of new medicinal compounds with specific therapeutic properties.
Used in Agrochemical Industry:
DMMA is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its role in these applications is to provide the necessary building blocks for the creation of effective and targeted agricultural products.
Used in Dye Industry:
In the dye industry, DMMA is employed as a key intermediate for the synthesis of various dyes. Its chemical properties enable the production of dyes with specific color characteristics and stability.
Used in Organic Chemistry Research:
(E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile is used as a versatile building block in organic chemistry research for the development of new organic compounds and the exploration of novel chemical reactions and mechanisms.

Upstream product

• 4102-53-8 4-iodo-2,6-dimethylaniline 
• 107-13-1 acrylonitrile 
• 88-05-1 2,4,6-trimethylaniline 
• 661489-23-2 (2E)-3-(4-amino-3,5-dimethylphenyl)prop-2-enenitrile hydrochloride 
• 87-62-7 2,6-dimethylaniline 
• 24596-19-8 4-bromo-2,6-dimethylphenylamine 
• 749249-96-5 C₁₁H₁₀N₂O₂ 
• 500292-92-2 (2E)-3-(4-amino-3,5-dimethylphenyl)prop-2-enamide 

Downstream Products

• 500287-72-9 rilpivirine 
• 1538550-43-4 (E)-3-(4-((2-chloropyrimidin-4-yl)amino)-3,5-dimethylphenyl)acrylonitrile 
• 700361-47-3 Rilpivirine hydrochloride 
• 1458666-40-4 (E)-4-((4-chloro-6-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)-1,3,5-triazin-2-yl)amino)benzonitrile 
• 1037445-51-4 C₂₄H₂₂N₆O 
• 1037445-47-8 C₂₂H₁₇ClN₆ 
• 749249-97-6 C₁₁H₁₄N₂ 

Relevant academic research and scientific papers

Synthetic method of rilpivirine intermediate

The invention provides a synthetic method of a rilpivirine intermediate. The synthesis method includes: taking 2, 4, 6-trimethylaniline as the raw material to react with 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) in a diluted hydrochloric acid solution

PROCESS FOR THE PREPARATION OF RILPIVIRINE

The present invention relates to a new process of preparation of Rilpivirine, or a pharmaceutically acceptable salt thereof. Another aspect of the invention concerns compounds of formulae II and III: and their salts thereof, and their use for the preparation of Rilpivirine or a suitable salt thereof.

Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles

Molecular hybridization is a powerful strategy in drug discovery. A series of novel diarylbenzopyrimidine (DABP) analogues were developed by the hybridization of FDA-approved drugs etravirine (ETR) and efavirenz (EFV) as potential HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs). Substituent modifications resulted in the identification of new DABPs with the combination of the strengths of the two drugs, especially compound 12d, which showed promising activity toward the EFV-resistant K103N mutant. 12d also had a favorable pharmacokinetic (PK) profile with liver microsome clearances of 14.4 μL/min/mg (human) and 33.2 μL/min/mg (rat) and an oral bioavailability of 15.5% in rat. However, its activity against the E138K mutant was still unsatisfactory; E138K is the most prevalent NNRTI resistance-associated mutant in ETR treatment. Further optimizations resulted in a highly potent compound (12z) with no substituents on the phenyl ring and a 2-methyl-6-nitro substitution pattern on the 4-cyanovinyl-2,6-disubstitued phenyl motif. The antiviral activity of this compound was much higher than those of ETR and EFV against the WT, E138K, and K103N variants (EC50 = 3.4, 4.3, and 3.6 nM, respectively), and the cytotoxicity was decreased while the selectivity index (SI) was increased. In particular, this compound exhibited acceptable intrinsic liver microsome stability (human, 34.5 μL/min/mg; rat, 33.2 μL/min/mg) and maintained the good PK profile of its parent compound EFV and showed an oral bioavailability of 16.5% in rat. Molecular docking and structure-activity relationship (SAR) analysis provided further insights into the binding of the DABPs with HIV-1 reverse transcriptase and provided a deeper understanding of the key structural features responsible for their interactions.

Pyrimidine heterocyclic compounds, pyrimidine heterocyclic compound salts, and preparation method and application thereof

The invention provides pyrimidine heterocyclic compounds, pyrimidine heterocyclic compound salts, and a preparation method and application thereof. According to the pyrimidine heterocyclic compounds provided by the invention, specific Rq is selected, so that the obtained compounds have favorable drug resistance and long half life when being used as the medicine for treating or preventing HIV. The compounds have the advantages of high activity, low toxicity and high stability.

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.

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)

MODIFIED HECK REACTION

The present invention includes a method for the preparation of a cinnamonitrile by addition of an aryl to acrylonitrile in the presence of a heterogeneous palladium catalyst, a phosphine, a base and a salt. The reaction can be conducted not only on aryl compounds activated with electron withdrawing groups, but also on neutral and even on deactivated aryl compounds.

HIV REPLICATION INHIBITING PURINE DERIVATIVES

The present invention relates to the use of a compound of formula (I) for the manufacture of a medicament for the prevention or the treatment of HIV infection wherein the compound of formula (I) is a compound of formula (I) a N-oxide, a pharmaceutically a

HIV INHIBITING 1,2,4-TRIAZINES

The present invention relates to HIV replication inhibitors of formula (I) as defined in the specification their use as a medicine, their processes for preparation and pharmaceutical compositions comprising them.