- Further Studies on a Site-specific Hydrogen Transfer Observed in Electron Capture Negative Ion Chemical Ionization Mass Spectrometry of Hydroxyamine Pentafluoropropionate Derivatives
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Further studies have demonstrated that the site-specific hydrogen transfer process involved in the formation of the m/z 145 anion of β-hydroxyamine pentafluoropropionate (PFP) derivatives observed under electron capture negative ion chemical ionization conditions occurs when the two functional groups are separated by up to five carbon atoms.Deuterium labelling has established that the site specificity, transfer of a hydrogen atom from the carbon adjacent to nitrogen to the OPFP group, is maintained in 4-amino-butan-1-ol-N,O-(PFP)2.The corresponding PFP derivatives of the N-methylaminoalkanol- (PFP)2 derivatives lack the m/z 145 species with m/z 163, -, being the base anion.Substitution of alkyl groups on the carbon adjacent to oxygen results in a diminution of the ion intensity at m/z 145 with a marked increase in the intensity of m/z 144.The formation of the m/z 145 and 144 anions is proposed to proceed through the intervention of a fluoride ion-molecule complex as outlined in Scheme 1 with the product ion distribution dependent on which of the two pathways is preferred.
- Low, G. K.-C.,Duffield, A. M.
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Read Online
- Method for synthesizing N-ethylethanolamine by micro-channel reactor
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The invention discloses a method for synthesizing N-ethylethanolamine by a micro-channel reactor. The method comprises the steps: adopting a Corning high-flux continuous flow micro-channel reactor, setting the flow velocity of the ethylene oxide aqueous solution to be 36.0-46.0mL/min and the flow velocity of the ethylamine aqueous solution to be 20.0mL/min, and respectively pumping the ethylene oxide aqueous solution and the ethylamine aqueous solution into the reactor to be preheated in a first module, that is, a straight-flow type preheating module, which has the temperature of 25-40 DEG C and is independent from each other; and then respectively making the solution enter a second module, that is, an enhanced mass transfer type mixing module, through an inlet A or an inlet B of the reactor, carrying out mixing reaction for 60-200 seconds at the temperature of 25-40 DEG C, and enabling the mixed liquid after the reaction to flow out from an outlet of the reactor; and collecting the output liquid of the micro-channel reaction device, and carrying out dehydrating to obtain the N-ethylethanolamine. The method has the advantages of short time, high efficiency, few byproducts, safety,stability and controllability, and the synthesized N-ethylethanolamine is suitable for pharmaceutical and chemical intermediates.
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Paragraph 0029; 0035-0037; 0043-0045; 0051-0053; 0059-0061
(2020/12/09)
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- Discovery of benzimidazole analogs as a novel interleukin-5 inhibitors
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A series of novel hydroxyethylaminomethylbenzimidazole analogs 5a-y were synthesized and evaluated for their IL-5 inhibitory activity using pro-B Y16 cell line. Among them, 2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino)butan-1-ol (5e, 94.3% inhibition at 30 μM, IC50 = 3.5 μM, cLogP = 4.132) and 3-cyclohexyl-2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino) propan-1-ol (5k, 94.7% inhibition at 30 μM, IC50 = 5.0 μM, cLogP = 6.253) showed the most potent inhibitory activity. The essential feature of SAR (Fig. 5) indicated that the chromenone ring can be replaced by a benzimidazole ring to maintain the inhibitory activity. In addition, the hydroxyethylaminomethyl group was suitable for the IL-5 inhibitory activity. Moreover, the hydrophobic substituents on carbon play an important role in the IL-5 inhibitory activity of these analogs. However, N-substituted analogs did not improve inhibitory activity. In addition, MTT assay of 5e and 5k with normal B lymphoblasts revealed that they had no significant effects on cell viability.
- Boggu, Pulla Reddy,Kim, Youngsoo,Jung, Sang-Hun
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- Hydrogenolysis of Amide Acetals and Iminium Esters
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Amide acetals and iminium esters were hydrogenated into amines under very mild reaction conditions over common hydrogenation catalysts. This finding provides a new strategy for the selective reduction of amides. The synthetic utility of this approach was demonstrated by the selective reduction of amides bearing ester and nitrile groups.
- Kadyrov, Renat
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p. 170 - 172
(2017/12/26)
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- METHOD FOR PRODUCING 2-(ALKYLAMINO)ETHANOL COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for effectively producing a 2-(alkylamino)ethanol compound from a N-alkyldiethanolamine compound. SOLUTION: A method for producing a 2-(alkylamino)ethanol compound in which a N-alkyldiethanolamine compound and an alkylamine compound are reacted under the presence of at least one metal catalyst selected from the group consisting of iron catalyst, copper catalyst, nickel catalyst, cobalt catalyst, palladium catalyst, platinum catalyst, silver catalyst, gold catalyst, osmium catalyst, iridium catalyst, ruthenium catalyst, and rhodium catalyst is provided. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0042
(2017/08/24)
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- Catalytic Hydrogenation for the Preparation of Amines from Amide Acetals, Ketene N,O-Acetals or Ester Imides
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The present invention relates to a process for the preparation of amines, comprising the following steps: Reaction of a (i) amide acetal of the general formula (I), or (ii) ketene N,O-acetal of the general formula (II), or (iii) ester imide of the general formula (III) with H2 in the presence of a hydrogenation catalyst, where catalyst and amide acetal or ketene N,O-acetal or ester imide are used in a molar ratio of from 1:10 to 1:100 000 and where a hydrogen pressure of from 0.1 bar to 200 bar is established and where a temperature in the range of from 0° C. to 250° C. is established.
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Paragraph 0153; 0154
(2016/10/04)
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- N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst
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Abstract: The mesoporous solid acid–base Cs–B–Zr mixed oxides were synthesized using the co-precipitation method followed by a subsequent thermal treatment. The catalytic activity of solid Cs–B–Zr mixed oxide was tested for solvent free acid–base catalysed direct alkylolamines with alcohols as green alkylating agent. The effects of Cs/B/Zr ratio, calcination temperature, reaction conditions, and reaction substrate on the catalytic performance of the catalysts were investigated. The XRD, N2 adsorption–desorption, ICP-OES, FT-IR and NH3/CO2-TPD results showed that the mesoporous structure and acid–base properties of the catalysts play important roles in the reaction. A suitable number of acid and basic sites on the catalyst lead to a high activity for the N-alkylation reaction. Graphical Abstract: A direct N-alkylation of amino alcohol with alcohols has been developed using mixed oxide Cs–B–Zr as an acid–base bifunctionalized catalyst.[Figure not available: see fulltext.]
- Chen, Aimin,Wang, Houyong,Liu, Rui,Bo, Yingying,Hu, Jun
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p. 1182 - 1193
(2016/07/06)
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- 2-(ETHYLAMINO)ETHANOL PRODUCTION METHOD
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The present invention relates to a production method for 2-(ethylamine) ethanol, including subjecting N-ethyldiethanolamine to a disproportionation reaction in the presence of at least one kind of catalyst selected from the group consisting of a manganese oxide catalyst and an alkali metal hydroxide-supporting zirconium oxide catalyst. According to the present invention, 2-(ethylamino)ethanol can be obtained by subjecting N-ethyldiethanolamine to the disproportionation reaction. 2-(Ethylamino)ethanol is a useful compound to be used in various applications such as a drug, an agricultural chemical, and a functional chemical.
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Paragraph 0027
(2015/09/23)
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- Pyrithione biocides enhanced by zinc metal ions and organic amines
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The present invention is directed to a stable, soluble, antimicrobial composition concentrate comprising pyrithione or a pyrithione complex in an amount of from about 0.5% to about 30 weight percent, a zinc source in an amount of from about 0.1% to about 10%, and an organic amine component in an amount of from about 30% to about 80%, said percents being based upon the total weight of the composition concentrate. The invention is also directed to methods of controlling the growth of free-living microorganisms or biofilms using the antimicrobial composition of the invention, and products made using the antimicrobial composition of the invention.
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- Detritylation of N-tritylamines via a naphthalene-catalyzed lithiation process
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The reaction of aliphatic and aromatic secondary and tertiary N-tritylamines 1 with lithium powder and a catalytic amount of naphthalene led to reductive detritylation, affording the corresponding amines 2 in good to excellent yields. The trityl group could selectively be removed in the presence of an allyl or a benzyl group. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalized N-tritylamines. The chemoselectivity between the trityl-nitrogen and the trityl-oxygen bond cleavages was also studied. This methodology represents an efficient deprotection of N-tritylamines under nonacidic reaction conditions.
- Behloul, Cherif,Guijarro, David,Yus, Miguel
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p. 1274 - 1280
(2007/10/03)
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- Analine derivatives as OSC inhibitors
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The present invention relates to compounds of formula (I) wherein U, Y, V, W, L, X, A1, A2, A3, A4, A5 and A6 are as defined in the description and claims and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasite infections, gallstones, tumors and/or hyperproliferative disorders, and/or treatment and/or prophylaxis of impaired glucose tolerance and diabetes.
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- 2,3-oxidosqualene-lanosterol cyclase inhibitors
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The present invention relates to piperidine derivatives useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, gallstones, tumors and/or hyperproliferative disorders, and treatment and/or prophylaxis of impaired glucose tolerance and diabetes.
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- Process for the continuous preparation of hydroxyalkylamides
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Process for the continuous preparation of hydroxyalkylamides Process for the continuous preparation of hydroxyalkylamides from carboxylic esters and alkanolamines, wherein the reaction of the starting materials is carried out in an extruder or intensive mixer by intensive mixing and brief reaction with supply of heat and simultaneous removal of the alcohol formed and the final product is then isolated.
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- Acid-Catalyzed Decomposition of 1-Alkyltriazolines: A Mechanistic Study
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1-Alkyltriazolines are five-membered cyclic triazenes containing the unusual Z-configuration for the triazene moiety.The hydrolytic decomposition of these compounds in aqueous or mixed acetonitrile-aqueous buffers leads predominantly to the formation of the corresponding 1-alkylaziridines and lesser amounts of 2-(alkylamino)ethanols, alkylamines, and acetaldehyde.The latter two products presumably result from hydrolysis of a rearrangement produkt, N-ethylidenealkylamine.Neither the nature of the 1-alkyl group nor the pH of the medium greatly influences the product distribution, although decomposition in purely aqueous buffers slightly reduces the aziridine yields.The rate of hydrolysis of 1-alkyltriazolines is about twice as fast as that of the analogous acyclic 1,3,3-trialkyltriazenes and varies in the order tert-butyl > isopropyl > ethyl > butyl > methyl > propyl > benzyl.The mechanism of the decomposition is specific acid-catalyzed (A1) involving rapid reversible protonation followed by rate-limiting formation of a 2-(alkylamino)ethyldiazonium ion.The slopes of the log kobs versus pH plots are near -1.0.The solvent deuterium isotope effect, kH2O/kD2O, is in all cases methyl > ethyl.
- Smith, Richard H.,Wladkowski, Brian D.,Taylor, Jesse E.,Thompson, Erin J.,Pruski, Brunon,et al.
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p. 2097 - 2103
(2007/10/02)
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- Catalysts for alkoxylation reactions
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Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF3 and metal alkyls or metal alkoxides, SiF4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.
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- Methods of alkoxylation
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Catalysts comprising mixtures of HF and metal alkoxides and mixed metal alkoxides produce a sharply peaked alkoxylation distribution during the alkoxylation of organic materials.
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- Catalysts for alkoxylation reactions
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Catalysts and a method of using said catalysts for the alkoxylation of a variety of materials is disclosed. Catalysts so described produce alkoxylates having a very sharp alkoxylate distribution. The catalysts are supported and unsupported dialkoxy and dialkyl metal fluorides and halides and alkyl metal difluorides and dihalides.
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- Reductive Alkylation of β-Alkanolamines with Carbonyl Compounds and Sodium Borohydride
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A synthesis of secondary alkylalkanolamines from primary alkanolamines in a rapid process in which overalkylation is virtually suppressed is described.The procedure combines the ease of formation of oxazolidines from alkanolamines with aldehydes or ketones in absolute ethanol and the lability of the newly formed C-O bond toward sodium borohydrode.The entire process is carried out in 15-35 min depending on the carbonyl substrate.
- Saavedra, Joseph E.
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p. 2271 - 2273
(2007/10/02)
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- Syntheses of α-C-Functionalized N-Nitrodialkylamines: Esters of methanol and 1-ethanol
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The α-acetoxynitramines 5 and 6 - important derivatives for studying the biological properties of N-nitrodialkylamines 4 - have been synthesized, and the stability of the ester bond has been investigated.The reaction of N-nitroalkylamines 7 with 1-halogenoethyl acetates 9, thought to afford 6, yielded the diazene N-oxides 10 as the main products.
- Plesch, Winfried,Wiessler, Manfred
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p. 1494 - 1503
(2007/10/02)
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- Anodic Oxidation of Amines. VII. Oxidation of β-Alkanolamines in Aqueous Buffer of pH 10
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The anodic oxidation of several different types of β-alkanolamines, R1R2C(OH)CR3R4NR5R6, was studied by cyclic voltammetry and controlled potential electrolysis in an aqueous carbonat buffer of pH 10 at a glassy carbon electrode.Upon oxidation, both the (α)C-(β)C and the C-N bonds are cleaved.Substituents R1-R4 affect the first oxidation potential and product distribution.The relative rates of the bond cleavages were estimated from the oxidation products.It was found that most of the amine cleaves through the (α)C-(β)C bond when at least one of the R groups is phenyl, nearly half cleaves through this bond when R is alkyl, and only about a tenth does so when R1-R4 are all hydrogen.The stability of the transient intermediates at the e-c step of the e-c-e process seems to affect the oxidation potentials and to govern the relative rates of the (α)C-(β)C bond cleavage.A scheme for the reaction processes is proposed.Keywords---β-alkanolamines; anodic oxidation; (α)C-(βC) bond fission; C-N bond fission; carbonate buffer; aldehyde; acetone; glycolaldehyde
- Masui, Masaichiro,Kamada, Yoshiyuki,Sasaki, Etuko,Ozaki, Shigeko
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p. 1234 - 1243
(2007/10/02)
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- Thiazolo-rifamycin derivatives and a method for their preparation
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Novel 4-desoxy-thiazolo[5,4-c]rifamycin SV derivatives having antibacterial activity and a method of preparing same by the reaction of rifamycin S with a cysteine derivative followed by the oxidation of the resulting product.
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