- 3 - Amino - 4 - bromophenol synthetic method
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The invention relates to a method for synthesizing 3-amino-4-bromophenol. The method comprises the following steps of: (1) diazotization reaction: dissolving 3-nitro-4-aminophenol used as a raw material into hydrobromic acid, and dropping a sodium nitrite aqueous solution at 0-10 DEG C for reacting for 1-3 hours to obtain a 3-nitrophenol-4-diazonium brine solution; (2) bromination reaction: dropping the solution obtained in the step (1) into a hydrobromic acid aqueous solution of cuprous bromide, stirring at 40-50 DEG C for reacting, and crystallizing and filtering to obtain a 3-nitro-4-bromophenol solid; and (3) reduction reaction: dissolving the solid obtained in the step (2) into alcohol, adding an iron oxide catalyst, heating up to 50-100 DEG C, and adding a hydrazine hydrate aqueous solution to the mixture for reacting for 2-5 hours to obtain the 3-amino-4-bromophenol. The synthesis method of the 3-amino-4-bromophenol has the advantages of reasonable design, moderate condition, easiness of operation and higher product yield and is suitable for industrial production.
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Paragraph 0007; 0016-0018
(2017/12/28)
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- The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions
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Abstract: 1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH2–CH2– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion. Graphical Abstract: [Figure not available: see fulltext.]
- Salmasi, Reihaneh,Gholizadeh, Mostafa,Salimi, Alireza,Garrison, Jered C.
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p. 2019 - 2028
(2016/09/16)
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- PRIMARY CARBOXAMIDES AS BTK INHIBITORS
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The invention provides carboxamide compounds of Formula (I) pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variable are defined herein. The compounds of the invention are useful for treating immunological and oncological conditions, including rheumatoid arthritis, juvenile rheumatoid arthritis, osteoarthritis, Crohn's disease, inflammatory bowel disease, ulcerative colitis, psoriatic arthritis, psoriasis, ankylosing spondylitis, interstitial cystitis, asthma, systemic lupus erythematosus, lupus nephritis, B cell chronic lymphocytic lymphoma, multiple sclerosis, chronic lymphocytic leukemia, small lymphocytic lymphoma, mantle cell lymphoma, B-cell non-Hodgkin's lymphoma, activated B-celllike diffuse large B-cell, lymphoma, multiple myeloma, diffuse large B-celllymphoma, follicular lymphoma, hairy cell leukemia or Lymphoblastic lymphoma.
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Page/Page column 264
(2015/01/16)
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- KAT II INHIBITORS
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The present invention relates to compounds 3-amino-1-hydroxy-2-oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile, 3-amino-1-hydxoxy-7-(2-methoxyethoxy)-3,4-dihydro-quinolin-2(1H)-one, and 3-amino-1-hydroxy-7-[(1S)-2-methoxy-1-methylethoxy]-3,4-dihydroquinolin-2(1H)-one, including racemic mixtures and resolved enantiomers thereof, to pharmaceutically acceptable salts thereof, and to the treatment of cognitive deficits associated with schizophrenia and other psychiatric, neurodegenerative and/or neurological disorders in mammals, including humans
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Page/Page column 24-25
(2012/06/16)
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- Rapid synthesis of diversely functionalized 3,4,7-trisubstituted indoles
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Synthetic approaches are described for the synthesis of 4-alkoxyindole-7-carboxamides and 4-alkoxy-3-cyanoindole-7-carboxamides, which are useful intermediates in medicinal chemistry research. Two strategies were employed, highlighted by a Bartoli indole synthesis or a sequential and regioselective use of chlorosulfonyl isocyanate to install both the 3-cyano and 7-carboxamido groups. These routes are scalable and afford diversely functionalized indoles for further elaboration.
- Grant, Seth W.,Gallagher, Timothy F.,Bobko, Mark A.,Duquenne, Celine,Axten, Jeffrey M.
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scheme or table
p. 3376 - 3378
(2011/06/28)
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- Mild, efficient, and regioselective monobromination of arylamines and phenols using [BBIm]Br3 as a new reagent
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We report here an efficient method for the synthesis and characterization of the room-temperature ionic liquid 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3) (2) and its application as an efficient reagent and solvent for regioselective bromination of arylamines and phenols under mild conditions. The bromination was carried out in the absence of organic solvents, and in most cases, the only extraction solvent needed was water. The spent 1,3-di-n-butylimidazolium bromide (1) was easily recycled.
- Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
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experimental part
p. 647 - 653
(2011/02/27)
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- An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent/solvent under mild conditions
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1-Butyl-3-methylpyridinium tribromide, [BMPy]Br3 proves to be a highly efficient, regioselective reagent/solvent for nuclear bromination of various anilines and phenols. The synthesis and characterization of the room temperature ionic liquid [BMPy]Br3 (2) is described. The bromination was carried out in the absence of organic solvents and in most cases the only extraction solvent needed was water. The spent 1-butyl-3-methylpyridinium bromide (1) was easily recycled.
- Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
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scheme or table
p. 1007 - 1009
(2009/05/11)
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- Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof
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The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (e.g., indazoles and benzothiazoles), which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 68
(2010/11/26)
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- 1 H-INDAZOLES, BENZOTHIAZOLES, 1,2-BENZOISOXAZOLES, 1,2-BENZOISOTHIAZOLES, AND CHROMONES AND PREPARATION AND USES THEREOF
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The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nAChR), activation of nAChRs, and the treatment of -disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (indazoles and benzothiazoles), which act as ligands for the α7 nAChR subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 77-78
(2010/11/27)
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- 2,3-Dimethoxybenzo[i]phenanthridines: Topoisomerase I-targeting anticancer agents
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Appropriately substituted benzo[i]phenanthridines structurally related to nitidine, a benzo[c]phenanthridine alkaloid with antitumor activity, are active as topoisomerase I-targeting agents. Studies on benzo[i]phenanthridines have indicated analogues that possess a 2,3-methylenedioxy moiety and at least one and preferably two methoxyl groups at the 8- and 9-positions, such as 8,9-dimethoxy-2,3-methylenedioxybenzo[i]phenanthridine, 2, are active as topoisomerase I-targeting agents. Tetramethoxylated benzo[i]phenanthridines, wherein the 2,3-methylenedioxy moiety is replaced with methoxyl groups at the 2- and 3-position, are inactive as a topoisomerase I-targeting agent. These results initially suggested that the 2,3-methylenedioxy moiety was critical to the retention of potent activity. Further studies revealed that 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine, 7a, is more potent than 2 as a topoisomerase I-targeting agent. The observation that 2,3-dimethoxylated benzo[i]phenanthridines can actually exhibit enhanced activity prompted the present study in which several 8-substituted 2,3-dimethoxybenzo[i]phenanthridines were prepared and their pharmacological activities evaluated. The influence of NH2, CN, CH2OH, OBn, OCH3, OH, and NHCOCH3substituents at the 8-position on the relative activity of these 2,3-dimethoxybenzo[i]phenanthridines was examined. Relative to these derivatives, 7a was the most potent topoisomerase I-targeting agent, possessing similar cytotoxicity to that of nitidine in the human lymphoblast tumor cell line, RPMI8402.
- Li, Dajie,Zhao, Baoping,Sim, Sai-Peng,Li, Tsai-Kun,Liu, Angela,Liu, Leroy F.,LaVoie, Edmond J.
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p. 521 - 528
(2007/10/03)
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- Trisubstituted carbocyclic cyclophilin binding compounds and their use
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The present invention relates to novel, non-peptidic small organic compounds having an affinity for cyclophilin (CyP)-type immunophilin proteins, and to pharmaceutical compositions comprising one or more of the said compounds. The invention further relates to the uses of these compounds and compositions for binding CyP-type proteins, inhibiting their peptidyl-prolyl isomerase activity, and for research, development, and therapeutic applications in a variety of medical disorders.
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- Optical element and compounds used in its manufacture
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An optical frequency conversion element has a wave-guiding layer which consists of a χ(2) -active ferroelectric liquid crystal. The monomeric or polymeric liquid crystal material has a periodic structure which permits the so-called quasi phase matching of a guided laser beam. The period length of the structure is equal to twice the coherence length lc =?/Δβ of the material, whereby Δβ=βo (2ω)-2βo (ω), with ω=angular frequency of the fundamental wave, 0=zero-order mode and β=propagation constant of the mode.
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- Heck reaction on solid support: Synthesis of indole analogs
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The intramolecular Heck reaction of polymer bound arylhalides such as 1 affords indole analogs 11 in high yield. The precursor is readily assembled from acid chlorides and allylic bromides and offers an approach to diverse libraries of indole analogs.
- Yun, Weiya,Mohan, Raju
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p. 7189 - 7192
(2007/10/03)
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