38336-04-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 3465, 1995 DOI: 10.1016/0040-4039(95)00527-J

Upstream product

• 151-56-4 ethyleneimine 
• 100-51-6 benzyl alcohol 
• 66021-75-8 ((2-azidoethoxy)methyl)benzene 
• 38336-06-0 N-benzyl-2-(benzyloxy)ethan-1-amine 
• 100-39-0 benzyl bromide 
• 141-43-5 ethanolamine 
• 100-44-7 benzyl chloride 
• 622-08-2 2-Benzyloxyethanol 
• 17229-17-3 benzyl 2-chloroethyl ether 
• 64-19-7 acetic acid 
• 634925-24-9 tert-butyl (2-(benzyloxy)ethyl)carbamate 
• 13620-31-0 benzyloxyacetonitrile 
• 87107-79-7 2-(2-(benzyloxy)ethyl)isoindoline-1,3-dione 
• 4981-83-3 2-(Benzyloxy)ethyl p-toluenesulfonate 

Downstream Products

• 66046-68-2 N-(2-benzyloxy-ethyl)-N'-(2-chloro-ethyl)-phosphorodiamidic acid but-3-enyl ester 
• 22283-20-1 N-(2-Benzyloxyethyl)-harnstoff 
• 51040-51-8 [1-(2-Benzyloxy-ethylcarbamoyl)-3-hydroxy-propyl]-carbamic acid benzyl ester 
• 50992-07-9 N-(2-Benzyloxy-ethyl)-2-dibenzylamino-4-hydroxy-butyramide 
• 50992-01-3 2-Benzamido-N-(2-benzyloxyaethyl)-4-hydroxybutyramid 
• 171779-78-5 N-(2-Benzyloxy-ethyl)-6-(2,2-dichloro-vinyl)-2,3-dimethoxy-benzamide 
• 1027972-80-0 (S)-N¹-[2-(2-Benzyloxy-ethylcarbamoyl)-2-hydroxy-1-methyl-ethyl]-2-[(S)-2-(3,3-dimethyl-butyrylamino)-3,3-dimethyl-butyrylamino]-N⁴,N⁴-dimethyl-succinamide 
• 200400-72-2 N-<2-(benzyloxy)ethyl>-2-<4-(3-pyridylcarbonyl)phenyl>-4-oxazolecarboxamide 
• 292072-97-0 rac-2-[(2-benzyloxyethyl)-thyminacetyl-amino]-cyclohexancarboxylic acid-(4-tert-butyl-cyclohexen-1-yl)-amide 

Relevant academic research and scientific papers

A N - benzyl ethanolamine preparation method

A N - benzyl ethanolamine preparation method, including the use of ethanolamine and benzyl chloride as the raw material, to solid phase alkali as the reaction of the acid and alkaline catalyst, in the 40 - 120 °C under stirring to carry out the condensation reaction, the reaction after the stop of the take methylethanone, the filtrate to carry out rectification under vacuum, collecting the fraction, product N - benzyl ethanolamine. This invention adopts the solid phase alkali to [...] and catalytic, through the solid-liquid two-phase are a temperature and reaction to improve the main the selectivity of the reaction, in order to improve the synthetic yield; compared with original craft, saves the sodium hydroxide solution used for washing with ethyl acetate extraction of complex process a plurality of times; at the same time as solid phase alkali acid and alkaline catalyst with hydrogen chloride the reaction generates sodium chloride, convenient recycling, realizes the zero discharge of waste water; improves the ethanolamine utilization rate of the raw material; the invention is not only simple and convenient operation, production process economic and environmental protection, few by-products, and the synthetic yield has been raised by 25 - 30%, preparation and reducing the cost to 30 - 35%.

Photoredox-Catalyzed Site-Selective α-C(sp3)?H Alkylation of Primary Amine Derivatives

The synthetic utility of tertiary amines to oxidatively generate α-amino radicals is well established, however, primary amines remain challenging because of competitive side reactions. This report describes the site-selective α-functionalization of primary amine derivatives through the generation of α-amino radical intermediates. Employing visible-light photoredox catalysis, primary sulfonamides are coupled with electron-deficient alkenes to efficiently and mildly construct C?C bonds. Interestingly, a divergence between intermolecular hydrogen-atom transfer (HAT) catalysis and intramolecular [1,5] HAT was observed through precise manipulation of the protecting group. This dichotomy was leveraged to achieve excellent α/δ site-selectivity.

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives

We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.

A method for the production of primary amines

The invention relates to the field of chemical industry and particularly relates to a method for preparing primary amine by using the raw materials including halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) and ammonia water (or formamide). The method comprises the following three steps: (1) imidization: 3,4-diarylfuran-2,5-diketone (I) reacts with ammonia (or formamide) and the like to obtain 3,4-diaryl-1H-pyrrole-2,5-diketone (II); (2) N-hydrocarbylation: 3,4-diaryl-1H-pyrrole-2,5-diketone (II) generates an N-hydrocarbylation reaction with halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) in the presence of alkali to obtain N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III); and (3) hydrolysis: N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III) is subjected to alkali hydrolysis to obtain primary amine and the generated 2,3-diaryl maleate is subjected to acid treatment and automatic ring closing to form 3,4-diaryl furan-2,5-diketone (I) which is subjected to imidization and directly applied to the N-hydrocarbylation reaction. The method provided by the invention has the characteristics that the 3,4-diaryl furan-2,5-diketone can be circularly used at a high recovery rate, the molar ratio of the raw materials is low, and the yield of the product primary amine is high.

An Iodine-Catalyzed Hofmann-L?ffler Reaction

Iodine reagents have been identified as economically and ecologically benign alternatives to transition metals, although their application as molecular catalysts in challenging C-H oxidation reactions has remained elusive. An attractive iodine oxidation catalysis is now shown to promote the convenient conversion of carbon-hydrogen bonds into carbon-nitrogen bonds with unprecedented complete selectivity. The reaction proceeds by two interlocked catalytic cycles comprising a radical chain reaction, which is initiated by visible light as energy source. This unorthodox synthetic strategy for the direct oxidative amination of alkyl groups has no biosynthetic precedence and provides an efficient and straightforward access to a general class of saturated nitrogenated heterocycles.

Synthesis and antitumor activity of 5-(5-halogenated-2-oxo-1H-pyrrolo[2,3-b]pyridin-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamides

We report herein the design and synthesis of a series of novel 5-halogenated-7-azaindolin-2-one derivatives containing a 2,4-dimethylpyrrole moiety. Nine target compounds with ≥70% inhibition against MCF-7 at 30 μM were further evaluated for their in vitro antitumor activity against seven human cancer cell lines by SRB assay. Results reveal that some compounds have potent antitumor activity, and the most active 13c7 (IC50s: 4.49-15.39 μM) was found to be more active than Sunitinib (IC50s: 4.70->30 μM) against all of the tested cancer cell lines.

Development of synthetic routes, via a tropinone intermediate, to a long-acting muscarinic antagonist for the treatment of respiratory disease

This contribution describes the development of two synthetic routes to an investigational muscarinic antagonist for the treatment of chronic obstructive pulmonary disease. The first route used a starting material which was in plentiful supply within the GSK network and was used to make material for early clinical trials and safety assessment studies. Further investigations identified a second, potential long-term manufacturing route from commercially available building blocks, using substrate control to install the two stereocentres with excellent selectivity. A key step was a substrate-directed epoxide reduction which also gave rise to a minor byproduct through a skeletal rearrangement of the tropane ring. A deuterium-labeling experiment was carried out, which shed light on the origin of the byproduct, and also guided the improvement of reaction conditions.

Synthesis and characterization of picket porphyrin receptors that bind phosphatidylglycerol, an anionic phospholipid found in bacterial membranes

The lipid binding ability of four urea-picket porphyrins designed to bind to both the phosphate anion portion as well as the glycerol hydroxyl groups of phosphatidylglycerol (PG) has been investigated. Isothermal titration calorimetry (ITC) and 1H NMR were used to determine the receptor's stoichiometry of binding, association constants, and both the enthalpy and entropy of binding with the PG anion. Spectral evidence shows that the phosphate anion portion of PG is hydrogen bonded to the urea groups of the receptors. This binding interaction orients the PG anion in the receptor pocket such that its glycerol hydroxyl groups can align with a third urea picket, and results are furnished that suggest this multifunctional interaction does occur. The structure of the entire picket was found to influence the enthalpy and entropy of lipid binding. The synthesis of tetrabutlyammonium phosphatidylglycerol (TBAPG), and a detailed spectral characterization of its headgroup, is also presented.

SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF

The invention is directed to compounds for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds, and methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, and/or accumulation or deficiency of O-GlcNAc.

PYRANO[3,2-D]THIAZOL DERIVATIVES AND USES THEREOF AS SELECTIVE GLYCOSIDASE INHIBITORS

Pyrano[3,2-d]thiazol derivatives of formula (I) for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds are disclosed. Methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc are also provided.