17061-62-0

Usage

Uses

Used in Pharmaceutical Synthesis:
BIS-(4-METHOXY-BENZYL)-AMINE is used as a reagent for the synthesis of pentanedioc acid derivatives, which are farnesyltransferase inhibitors. These inhibitors play a significant role in the development of drugs targeting enzymes involved in various diseases.
Used in Antiviral Drug Development:
In the field of antiviral research, BIS-(4-METHOXY-BENZYL)-AMINE is utilized in the preparation of (heteroarylamino)triazolamines. These compounds exhibit antiviral properties, making them useful in the treatment of Hepatitis C virus (HCV) infection, offering potential therapeutic solutions for patients suffering from this viral disease.

InChI:InChI=1S/C16H19NO2/c1-18-15-7-3-13(4-8-15)11-17-12-14-5-9-16(19-2)10-6-14/h3-10,17H,11-12H2,1-2H3

Upstream product

• 3717-21-3 (E)-4-methoxybenzaldoxime 
• 3261-60-7 N-(4-methoxybenzylidene)-4-methoxybenzylamine 
• 108-94-1 cyclohexanone 
• 874-90-8 4-methoxybenzonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 64-17-5 ethanol 
• 141-78-6 ethyl acetate 
• 64-19-7 acetic acid 
• 2746-25-0 p-Methoxybenzyl bromide 
• 2393-23-9 4-methoxy-benzylamine 
• 3261-60-7 (E)-N-(4-methoxybenzylidene)-1-(4-methoxyphenyl)methanamine 
• 104-94-9 4-methoxy-aniline 
• 119208-80-9 1,3,5-tris(4-methoxyphenyl)-2,4-diazapenta-1,4-diene 

Downstream Products

• 103643-09-0 bis-(4-methoxy-benzyl)-(2-piperidino-ethyl)-amine 
• 103509-46-2 bis-(4-methoxy-benzyl)-(2-morpholin-4-yl-ethyl)-amine 
• 133777-96-5 N,N-bis<(4-methoxyphenyl)methyl>ethenesulfonamide 
• 180747-36-8 2-Bromo-N,N-bis-(4-methoxy-benzyl)-acetamide 
• 531504-19-5 6-chloro-N²,N²-bis-(4-methoxy-benzyl)-N⁴-(4-methoxy-phenyl)-pyrimidine-2,4-diamine 
• 244288-51-5 2-amino-4-chloro-6-di(4-methoxybenzyl)-amino-5-pyrimidine carbaldehyde 
• 656223-61-9 (S)-N,N-bis-p-methoxybenzyl(cyclohex-2-enyl)amine 
• 803727-82-4 N,N-bis-(4-methoxyphenylmethyl)-(benzenemethane)sulfonamide 
• 945618-65-5 6-chloro-N⁴,N⁴-bis(4-methoxybenzyl)-N²-(4-methoxyphenyl)pyrimidine-2,4-diamine 
• 945618-67-7 6-(cyclohexylmethoxy)-N⁴,N⁴-bis(4-methoxybenzyl)-N²-(4-methoxyphenyl)pyrimidine-2,4-diamine 
• 811794-13-5 2-(1,3-dioxoisoindolin-2-yl)-N,N-bis(4-methoxybenzyl)ethanesulfonamide 
• 903578-46-1 4-bromo-2-fluoro-N,N-bis[(4-methoxyphenyl)methyl]benzenesulfonamide 
• 884004-38-0 6-chloro-N,N-bis[(4-methoxyphenyl)methyl]-5-(trifluoromethyl)pyridin-2-amine 

Relevant academic research and scientific papers

Synthesis, spectral, crystal structures, Hirshfeld surface analysis and DFT studies on bis(N,N-di(4-methoxybenzyl)dithiocarbamato-S,S′)zinc(II) and its imine adducts: new precursor for the preparation of hexagonal ZnS

[Zn(4-mbzdtc)2] (1), [Zn(4-mbzdtc)2(py)] (2), [Zn2(4-mbzdtc)4(4,4′-bipy)] (3), and [Zn(4-mbzdtc)2(2,2′-bipy)] (4), (where, 4-mbzdtc = N,N-di(4-methoxybenzyl)dithiocarbamate) were prepared and characte

Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions

A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis

The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.

Platinum Nanoparticles Uniformly Dispersed on Covalent Organic Framework Supports for Selective Synthesis of Secondary Amines

Covalent organic frameworks (COFs) with pore structures are talented supports for active components. In this report, COF has been rationally fabricated and served as host for growing uniformly dispersed platinum nanoparticles with a narrow size distribution (2 nm). The obtained hybrid Pt/COF exhibits high catalytic activity in the reductive amination of benzaldehyde towards secondary amines with a yield of 96 % and good recyclability. The preferable selectivity towards secondary amines could be attributed to synergistic effects of active platinum nanoparticles and COF, in which metallic Pt nanoparticles were uniformly dispersed with a positively charged surface. This work will open an avenue towards controlling the interaction between active metals and support as well as rational design of catalysts for demanding transformations for fine agrochemicals intermediates.

Photo-Electroswitchable Arylaminoazobenzenes

Azobenzenes appended with a redox-active arylamino group (redox auxiliary, RA) are prepared and shown to undergo fast, complete, and catalytic Z→E azo isomerization upon electron loss from the RA unit of the azobenzene. The RA-azo structures can be reversibly (E→Z→E)n cycled by sequential photo- and electrostimulation. Due to the robust nature of the RA?+-azo radical cation chain carrying species, initiation of electron transfer (ET) catalysis occurs at low levels (1.0-0.04 mol %) of catalytic loading and is effective even at Z-RA-azo concentrations of 10-4-10-5 M, yielding TONs (turnover numbers) of 100-2300 under such dilute conditions. The RA-azo Z→E conversion is demonstrated using chemical oxidation (redox switching), electrochemical oxidation (electro switching), and photochemical oxidation (photoredox switching). The Z→E acceleration is shown to be at least 2 × 109-fold for RA-azo 5. DFT calculations on methyl yellow suggest that a N-centered radical cation of the RA group stabilizes the Z→E N-N twist transition state of the RA?+-azo, yielding a large reduction in the barrier for RA?+-azo compared to neutral RA-azo. The RA-azo structure class has nanomechanical features that can be toggled with photo- and electrostimulation, the latter offering a quick switch for complete Z→E conversion.

Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt?CuFe/Fe3O4 Catalyst and Ammonia Borane as Hydrogen Donor

Hydrogenation of nitriles is an efficient and environmentally friendly route to synthesize symmetrical secondary amines, but it usually produces a mixture of amines, imines, and hydrogenolysis by-products. Herein we report a magnetic quaternary-component Pt?CuFe/Fe3O4 nanocatalyst system for the selective synthesis of symmetrical secondary amines with ammonia borane as hydrogen donor. The catalyst with a low Pt loading (0.456 wt%) is the source of the activity, and the d-band electron transfer from Cu to Fe enhances the selectivity. This synergistic effect results in the transformation of benzonitrile to dibenzylamine with excellent conversion (up to 99 %) and nearly quantitative selectivity (up to 96 %) under mild reaction conditions, nevertheless, the reaction TOF is as high as up to 1409.9 h?1. A variety of nitriles are suitable for the synthesis of symmetrical secondary amines. More importantly, unwanted hydrogenolysis byproducts, especially toluene, is not detected at all. In addition, the catalyst is magnetically recoverable, and it can be reused up to five times.

Discovery of novel VX-809 hybrid derivatives as F508del-CFTR correctors by molecular modeling, chemical synthesis and biological assays

Cystic fibrosis (CF) is the autosomal recessive disorder most recurrent in Caucasian populations. It is caused by different mutations in the cystic fibrosis transmembrane regulator protein (CFTR) gene, with F508del being the most common. During the last y

Pd/TiO2-Photocatalyzed Self-Condensation of Primary Amines to Afford Secondary Amines at Ambient Temperature

Symmetric secondary amines were synthesized by the self-condensation of primary amines over a palladium-loaded titanium dioxide (Pd/TiO2) photocatalyst. The reactions afforded a series of secondary amines in moderate to excellent isolated yields at ambient temperature (30 °C, in cyclopentyl methyl ether). Applicability for one-pot pharmaceutical synthesis was demonstrated by a photocatalytic reaction sequence of self-condensation of an amine followed by N-alkylation of the resulting secondary amine with an alcohol.

An intramolecular C(sp3)-H imination using PhI-m CPBA

Herein, a highly exothermic primary amine-polyvalent iodine reaction has been used successfully for selective functionalization of acidic C(sp3)-H groups for a dehydrogenative C-H imination reaction by 4H elimination. Overall, C(sp3)-H imination at 1,5 distances was readily done via organocatalysis using PhI (10 mol%)-mCPBA under ambient conditions.

SUBSTITUTED PYRIMIDINONES AS AGONISTS OF THE APJ RECEPTOR

Compounds of Formula I and Formula II, pharmaceutically acceptable salts thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: Figure I and Figure II where the definitions of the variables are provided herein.