13519-74-9

Upstream product

• 4301-72-8 N-ethyl-2-chloro-N-nitroso-aniline 
• 64-67-5 diethyl sulfate 
• 95-51-2 o-chloroaniline 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 64-17-5 ethanol 
• 88-73-3 2-Chloronitrobenzene 
• 103-69-5 N-ethyl-N-phenylamine 
• 74-85-1 ethene 
• 2596-93-2 2-chloro-N-phenylformamide 
• 35224-54-5 N-(2-chloro-phenyl)-alanine 
• 121-44-8 triethylamine 

Downstream Products

• 123282-60-0 N-ethyl-N-(2-chloro-phenyl)-N'-phenyl-benzamidine 
• 1404508-90-2 N-(2-chlorophenyl)-N-ethylethenesulfonamide 
• 81416-26-4 N-(2-chlorophenyl)pyridin-2-amine 
• 136343-78-7 2-(o-chloro-N-ethylanilino)pyridine 
• 67103-38-2 C₁₉H₁₇ClN₂O₄ 
• 35517-99-8 C₉H₉Cl₂NS 
• 55239-34-4 C₉H₉Cl₂NO 

Relevant academic research and scientific papers

Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy

Hormone therapy targeting estrogen receptors is widely used clinically for the treatment of breast cancer, such as tamoxifen, but most of them are partial agonists, which can cause serious side effects after long-term use. The use of selective estrogen receptor down-regulators (SERDs) may be an effective alternative to breast cancer therapy by directly degrading ERα protein to shut down ERα signaling. However, the solely clinically used SERD fulvestrant, is low orally bioavailable and requires intravenous injection, which severely limits its clinical application. On the other hand, double- or multi-target conjugates, which are able to synergize antitumor activity by different pathways, thus may enhance therapeutic effect in comparison with single targeted therapy. In this study, we designed and synthesized a series of novel dual-functional conjugates targeting both ERα degradation and histone deacetylase inhibiton by combining a privileged SERD skeleton 7-oxabicyclo[2.2.1]heptane sulfonamide (OBHSA) with a histone deacetylase inhibitor side chain. We found that substituents on both the sulfonamide nitrogen and phenyl group of OBHSA unit had significant effect on biological activities. Among them, conjugate 16i with N-methyl and naphthyl groups exhibited potent antiproliferative activity against MCF-7 cells, and excellent ERα degradation activity and HDACs inhibitory ability. A further molecular docking study indicated the interaction patterns of these conjugates with ERα, which may provide guidance to design novel SERDs or PROTAC-like SERDs for breast cancer therapy.

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex

Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.

Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines

The first general and efficient cobalt-catalyzed deoxygenative hydrogenation of amides to amines is presented. The optimal catalytic system based on a combination of [Co(NTf2)2] and (p-anisyl)triphos (L3) in the presence of [Me3SiOTf] as acidic co-catalyst facilitates the direct hydrogenation of a broad range of amides to the corresponding amines under mild conditions. A set of control experiments indicate that, after the initial reduction of the amide carboxylic group to the well-known hemiaminal intermediate, the reaction mainly proceeds through C-O bond cleavage though other pathways might be also involved to a minor extent. This journal is

Ru-Catalyzed Deoxygenative Transfer Hydrogenation of Amides to Amines with Formic Acid/Triethylamine

A ruthenium(II)-catalyzed deoxygenative transfer hydrogenation of amides to amines using HCO2H/NEt3 as the reducing agent is reported for the first time. The catalyst system consisting of [Ru(2-methylallyl)2(COD)], 1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) and Bis(trifluoromethane sulfonimide) (HNTf2) performed well for deoxygenative reduction of various secondary and tertiary amides into the corresponding amines in high yields with excellent selectivities, and exhibits high tolerance toward functional groups including those that are reduction-sensitive. The choice of hydrogen source and acid co-catalyst is critical for catalysis. Mechanistic studies suggest that the reductive amination of the in situ generated alcohol and amine via borrowing hydrogen is the dominant pathway. (Figure presented.).

B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane

The first B(C6F5)3-catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal-free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction-sensitive were well tolerated. This new method is also applicable to chiral amide substrates without erosion of the enantiomeric purity. The role of BF3 ? OEt2 co-catalyst in this reaction is to activate the amide carbonyl group via the in situ formation of an amide-boron adduct. (Figure presented.).

Hydrogenation and: N-Alkylation of anilines and imines via transfer hydrogenation with homogeneous nickel compounds

The nickel-catalyzed N-Alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the CN bond reduction and N-Alkylation of a variety of imines with ethanol, the latter acting as a hydrogen and acetaldehyde source, which allowed for the reduction and subsequent condensation to yield the corresponding N-Alkylated products.

A sound shielding through the level three-stage amine instead new method should be secondary amine

The invention discloses a novel method for preparing secondary amine by a reaction of primary amine and tertiary amine. The method comprises the following steps of 1, adding primary amine and tertiary amine into a reaction container according to a mole ratio of primary amine to tertiary amine of 1: 3, adding [(Bt)2*Ir*P(nBu)3]OTf as a catalyst (wherein Bt represents phenylbenzothiazole) into the reaction container, adding an organic solvent into the reaction container, and carrying out a reaction process at a temperature of 120-160 DEG C for 6-12h, wherein a mole ratio of primary amine, tertiary amine to catalyst is 1: 3: 0.01, and 2, carrying out purification by a silica gel column of 200-300 meshes, pre-leaching the silica gel column by 20-50mL of petroleum ether, carrying out elution on the leacheate at a leacheate flowing rate of 1-2mL/min for 3-6h so that the solvent is removed and the corresponding secondary amine product is obtained. A research result shows that the novel method for producing secondary amine by a reaction of primary amine and tertiary amine has the characteristics of mild conditions, high conversion rate and no pollutant. The method solves the problems of the existing secondary amine synthesis method and improves secondary amine synthesis.

Deoxygenative Hydrogenation of Amides Catalyzed by a Well-Defined Iridium Pincer Complex

The iridium-catalyzed highly chemoselective hydrogenation of amides to amines has been developed. Using a well-defined iridium catalyst bearing a P(O)C(O)P pincer ligand combined with B(C6F5)3, the C-O cleavage products are formed under mild reaction conditions. The reaction provides a new method for the preparation of amines from amides in good yield with high selectivity.

Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines

A broad range of secondary and tertiary amides has been hydrogenated to the corresponding amines under mild conditions using an in situ catalyst generated by combining [Ru(acac)3], 1,1,1-tris(diphenylphosphinomethyl)ethane (Triphos) and Yb(OTf)3. The presence of the metal triflate allows to mitigate reaction conditions compared to previous reports thus improving yields and selectivities in the desired amines. The excellent isolated yields of two scale-up experiments corroborate the feasibility of the reaction protocol. Control experiments indicate that, after the initial reduction of the amide carbonyl group, the reaction proceeds through the reductive amination of the alcohol with the amine arising from collapse of the intermediate hemiaminal.