2933-81-5

Upstream product

• 25217-18-9 1-chloro-2-(4-chloro-phenylcarbamoyloxy)-ethane 
• 106-47-8 4-chloro-aniline 
• 107-07-3 2-chloro-ethanol 
• 7462-17-1 2-(4-chlorophenoxy)-N-(2-hydroxyethyl)acetamide 
• 52316-60-6 2-hydroxyethylchloramine 
• 108-90-7 chlorobenzene 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 96-49-1 [1,3]-dioxolan-2-one 
• 106-39-8 bromochlorobenzene 
• 141-43-5 ethanolamine 
• 107-21-1 ethylene glycol 
• 5198-49-2 3-(4-chloro-phenyl)-oxazolidin-2-one 
• 637-87-6 1-Chloro-4-iodobenzene 

Downstream Products

• 32974-60-0 (4-chloro-phenyl)-[3-(4-chloro-phenyl)-oxazolidin-2-ylidene]-amine 
• 19853-57-7 3-(4-chloro-phenyl)-2-phenyl-[1,3,2]oxazaphospholidine 
• 32725-16-9 4-(4-chloro-phenyl)-morpholine-2,3-dione 
• 5198-49-2 3-(4-chloro-phenyl)-oxazolidin-2-one 
• 1374779-29-9 C₂₉H₂₆Cl₂N₂O₅S 
• 1608459-95-5 C₁₃H₁₈ClNO₃ 
• 13452-26-1 3-(4-chloro-phenyl)-oxazolidine 
• 4902-32-3 2-((4-chlorophenyl)(methyl)amino)ethan-1-ol 

Relevant academic research and scientific papers

Green synthesis of N-(2-hydroxyethyl)anilines by the selective alkylation reaction in H2O

Based on our previous work, a safer and more sustainable protocol for the synthesis of N-(2-Hydroxyethyl)anilines has been developed. The synthesis included the selective alkylation reaction of aniline with 2-chloroethanol in H2O, eliminating the need for any catalysts and solvents during synthesis. Comparing with our previous work, the salient features of this methodology are eco-friendliness, economic benefit, and the ease of obtaining target compounds. The selective alkylation reaction in H2O is amenable to scale-up for the synthesis of N-(2-Hydroxyethyl)anilines.

Cu2O/1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide catalyzed C-N cross-coupling reaction in aqueous media

An experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of imidazole, indole, pyrrole, alkyl alcohol amines, and alkyl amines with aryl iodides and bromides. The reaction proceeds in water-ethanol media at 120 °C for 12 h with Cu2O as the catalyst, 1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide (L2) as the ligand, NaOH as the base to generate a wide range of N-arylated products in moderate to excellent yields. Aqueous medium, ease of operation, and broad substrate scope give the process a benign environmental profile.

Amide compound for prevention and treatment of mental disorders

The present invention relates to an amide compound for prevention and treatment of mental disorders, which is shown as a formula (I), a pharmaceutically acceptable salt thereof, a prodrug thereof, a solvate thereof, a deuterated substance or a stereoisomer thereof. Wherein R1, R2, R3, R4, R5, Ar1, Ar2, p and q are as defined in the specification. The invention also relates to a preparation methodof the amide compound, a pharmaceutical composition and a pharmaceutical preparation containing the amide compound, and an application of the compound in preparation of a drug for prevention or treatment of mental disorders such as depression, depression and anxiety, and schizophrenia.

Palladium-catalyzed intramolecular carbene insertion into C(sp3)-H bonds

A palladium-catalyzed carbene insertion into C(sp3)-H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd0 and PdII, is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium-catalyzed C(sp3)-C(sp3) bond assembly starting from diazocarbonyl compounds. DFT calculations revealed that this direct C(sp3)-H bond functionalization reaction involves an unprecedented concerted metalation-deprotonation step. Pd in action: Palladium has been used to catalyze the C(sp3)-H insertion of metal carbenoids derived from α-diazoesters to form pyrrolidines through intramolecular assembly of C(sp3)-C(sp3) bonds. A reaction mechanism involving a metalation-deprotonation step instead of the usual concerted but asynchronous process is proposed.

N-Arylazetidines: Preparation through Anionic Ring Closure

We report herein an efficient synthesis of diversely substituted N-aryl-2-cyanoazetidines based on an anionic ring-closure reaction. These compounds can be prepared from β-amino alcohols in enantiomerically pure form through a three-step sequence involving (i) copper-catalyzed N-arylation, (ii) N-cyanomethylation of the secondary aniline, and (iii) one-pot mesylation followed by ring closure induced by a base. This high-yielding sequence gives access to azetidines with a predictable and adjustable substitution pattern and also with predictable diastereoselectivity. These compounds are susceptible to multiple further derivatizations through Suzuki coupling or nitrile transformation, thus appearing as valuable new scaffolds for medicinal chemistry. Their rigid shape, featuring an almost planar N-arylamine and a planar four-membered ring, was revealed by both AM1 calculations and X-ray crystallography.

TRICYCLIC PIPERAZINE DERIVATIVE

Disclosed are compounds useful as inhibitors of Phosphodiesterase 1 (PDE1), compositions thereof, and methods of using the same.

Bis-aryl urea derivatives as potent and selective LIM kinase (Limk) inhibitors

The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 1 μM), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 μM inhibited only Limk1 and STK16 with ≥80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. 1H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.

Green and efficient protocol for the synthesis of N-(2-hydroxyethyl)anilines by the alkylation reaction in ionic liquid

A green and efficient protocol for the synthesis of N-(2-hydroxyethyl)anilines by the selective alkylation reaction in ionic liquid [BMIM]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) has been developed, eliminating the need for toxic and expensive catalysts and volatile organic solvents. The effects of the amount of ionic liquid, temperature, time, and substrate structure on the reaction were investigated. The conversion and selectivity of N-(2-hydroxyethyl)anilines obtained in ionic liquid [BMIM]BF4 are significantly increased in comparison to those traditional methods. Furthermore, the ionic liquid could be easily separated and reused at least five times. It provided a simple and efficient alternative way for the industrial synthesis of N-(2-hydroxyethyl)anilines.

CONTROLLED HNO RELEASE THROUGH INTRAMOLECULAR CYCLIZATION-ELIMINATION

Protected HNO donors designed to undergo non-enzymatic release at neutral pH via an intramolecular cyclization-elimination are disclosed. The rate of cyclization, and therefore HNO release, can be controlled by substituents and chain length. Thus, biologi