74906-16-4

Upstream product

• 106-47-8 4-chloro-aniline 
• 5147-80-8 [Bis(methylthio)methylene]malononitrile 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 109-77-3 malononitrile 
• 74-88-4 methyl iodide 

Downstream Products

• 1000286-78-1 4-amino-3-(4-chlorophenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine 
• 101460-19-9 5-cyano-2,6-diamino-4-p-chloroanilinopyrimidine 
• 130224-49-6 4-amino-3-(p-chlorophenylamino)pyrazolo<3,4-d>pyrimidine 
• 197805-17-7 4-amino-5-benzoyl-1-(4-chloro-phenyl)-2-methoxy-pyrrole-3-carbonitrile 
• 197805-19-9 4-amino-1-(4-chloro-phenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile 
• 197805-16-6 [3-(4-chloro-phenyl)-5-phenyl-3H-oxazol-2-ylidene]malononitrile 
• 116991-82-3 5-<1-Cyano-2-(4-chlorophenylamino)-2-methylthioethenyl>tetrazole 
• 130224-43-0 5-amino-3-(4-chlorophenylamino)pyrazole-4-carbonitrile 

Relevant academic research and scientific papers

Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines

Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of α-functionalized-β-anilino-β-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the β-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.

Utility of bis(methylthio)methylene malononitrile as a synthon in the synthesis of new poly-functionalized cyanoiminopyrimidines

Abstract: A new series of 4-(alkyl/arylamino)-6-amino-5-cyano-2-cyanoimino-1H-pyrimidine was obtained via one-pot three-component reaction of bis(methylthio)methylene malononitrile, primary amines, and cyanoguanidine using sodium ethoxide as basic catalys

A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation

A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.

One-pot synthesis of functionalized tetrahydro-1,4-thiazepines

One-pot synthesis of (5Z,7Z)-5-amino-7-(ethyl or arylimino)-2,3,4,7- tetrahydro-1,4-thiazepine-6-carbonitriles from cyclocondensation of 2-((ethyl or arylamino)(mercapto)methylene)malononitrile potassium salts or their methylated derivatives with 2-chloro

One-pot synthesis of 6-substituted amino-2,4-diaminopyrimidine derivatives using ketene dithioacetals with amines and guanidine carbonate

6-Substituted amino-2,4-diaminopyrimidine derivatives were prepared by one-pot synthesis using ketene dithioacetals, amine compounds, and guanidine carbonate in pyridine. These pyrimidine products displayed blue fluorescence in the solid state.

New Syntheses of 2,4-Diaminopyrroles and Aminopyrrolinones

Oxazolin-2-ylidene-malononitriles 3a-d, obtainable from thioketenaminals and α-halogen-ketones, react with primary and secondary amines to afford 2,4-diamino-pyrroles 5a-h. Mercaptobenzen as nucleophilic agent gives the 4-amino-2-phenylthio-pyrrole 5j. Analogously, cyano-(3,5-diphenyl-3H-oxazol-2-ylidene)-acetic acid methyl esters were prepared as intermediates for the synthesis of 2-amino-4-oxo-pyrrolines 10a-d. The isomeric 4-amino-2-oxo-pyrrolines 13a-d can be obtained from 4-amino-2-methoxy-pyrroles, which serves as proof for the position of substituents. The structures were investigated by 1H and 13C NMR spectroscopy.