- New synthesis process of 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester
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The invention relates to a new synthesis process of 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester( as shown in the formula I). The new synthesis process comprises the following steps that (1) tetrahydropyranone (as shown in the formula II) is condensed with hydrazine hydrate to generate a product, namely hydrazone (as shown in the formula III); (2) under alkaline conditions, the hydrazone (asshown in the formula III) reacts with iodine to generate a compound 4-iodo-3,6-dihydro-2H-pyran (as shown in the formula IV); (3) the compound IV and a Grignard reagent are in a Grignard exchange reaction, and then coupled with isopropoxyboronic acid pinacol ester (as shown in the formula V) to prepare a target product, namely the 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester. The synthesis process disclosed by the invention is high in yield, mild in reaction conditions, and suitable for large-scale industrial production.
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- TETRAHYDROISOQUINOLINE DERIVED PRMT5-INHIBITORS
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A compound of formula I wherein: n is 1 or 2: p is 0 or 1; R1 is optionally one or more halo or methyl groups; R2a and R2b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R2c and R2d are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R3a and R3b are independently selected from H and Me; R4 is either H or Me; R5 is either H or Me; R6a and R6b are independently selected from H and Me; A is either (i) optionally substituted phenyl; (ii) optionally substituted naphthyl; or (iii) optionally substituted C5-12 heteroaryl.
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- 5-Alkyl-2-urea-Substituted Pyridines: Identification of Efficacious Glucokinase Activators with Improved Properties
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Two 1-(4-aryl-5-alkyl-pyridin-2-yl)-3-methylurea glucokinase activators were identified with robust in vivo efficacy. These two compounds possessed higher solubilities than the previously identified triaryl compounds (i.e., AM-2394). Structure-activity re
- Kohn, Todd J.,Du, Xiaohui,Lai, Sujen,Xiong, Yumei,Komorowski, Renee,Veniant, Murielle,Fu, Zice,Jiao, Xianyun,Pattaropong, Vatee,Chow, David,Cardozo, Mario,Jin, Lixia,Conn, Marion,DeWolf, Walter E.,Kraser, Christopher F.,Hinklin, Ronald J.,Boys, Mark L.,Medina, Julio C.,Houze, Jonathan,Dransfield, Paul,Coward, Peter
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p. 666 - 670
(2016/07/26)
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- Method for synthesizing 3, 6-dihydro-2H-pyrazine (thiazine) furan-4-boric acid ester
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The invention discloses a method for synthesizing 3, 6-dihydro-2H-pyrazine (thiazine) furan-4-boric acid ester. According to the method, tetrahydropyrazole (thiazine) furan-4-ketone serves as the raw material, generates hydrazone with p-toluenesulfonhydrazide, then reacts with NBS/organic alkali to generate alkenyl bromide and next forms Grignard reagent with magnesium metal, after the Grignard reagent is formed, boron reagent is added for a reaction, and the 3, 6-dihydro-2H-pyrazine (thiazine) furan-4-boric acid ester is obtained. By means of the method, ultralow temperature, column chromatography and palladium catalyzed coupling in a literature method are avoided, raw materials are easy to obtain, cost is low, conditions are mild, and the method has potential industrial application and amplification prospect.
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- A 3,6-dihydro -2H-pyran-4-boronic acid frequency method for the synthesis of ester
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The invention discloses a synthetic method of 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester, which comprises the following steps: 1) carrying out a reaction of tetrahydro-4H-pyran-4-one and hydrazine hydrate in a solvent to generate single ketone hydrazone; 2) carrying out a reaction of the single ketone hydrazone and copper bromide in a solvent in the presence of triethylamine to obtain a dibromo intermediate; 3) carrying out an elimination reaction of the dibromo intermediate and an alkali in a solvent to obtain an alkenyl bromide compound; 4) carrying out a Suzuki-Miyaura reaction of the alkenyl bromide compound and bis(pinacolato)diboron in a solvent in the presence of a palladium complex to obtain the product. The synthetic method of the invention is simple, and low in cost, adopts no dangerous raw materials, and is safe and suitable for large-scale production.
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- Development of an efficient process for 3,6-dihydro-2h-pyran-4-boronic acid pinacol ester
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An efficient process for the synthesis of 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester has been developed in one-pot manner. Starting from the condensation of 4-tetrahydropyranone with hydrazine hydrate, the subsequent treatment of hydrazone with copper(II) bromide-triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) conveniently gave 4-bromo-3,6-dihydro-2H-pyran, which was then conducted through palladium-catalyzed borylation to afford the desired product using a low loading of a Pd catalyst.
- Xue, Feng,Zhu, Yong,Li, Chang-Gong
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p. 1654 - 1659
(2015/09/28)
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- Novel Heterocyclic Compounds and Uses Thereof
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New substituted heterocyclic compounds, compositions containing them, and methods of using them for the inhibition of Raf kinase activity are provided. The new compounds and compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.
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- NOVEL PYRIDINE DERIVATIVES
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The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
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- PYRIDIN- 2 -AMIDES USEFUL AS CB2 AGONISTS
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The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
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- AKT INHIBITORS
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The present invention provides AKT inhibitors of the formula: Formula I The present invention also provides pharmaceutical compositions comprising compounds of Formula I, uses of compounds of Formula I and method of using compounds of Formula I.
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Page/Page column 108
(2011/05/06)
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- HETEROCYCLIC COMPOUNDS AND THEIR USES
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Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjogren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity, The present invention also enables methods for treating cancers that are mediated, dependent on or associated with p110δ activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia (T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.
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Page/Page column 105
(2011/01/05)
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- α-Hydroxyalkyl heterocycles via chiral allylic boronates: Pd-catalyzed borylation leading to a formal enantioselective isomerization of allylic ether and amine
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(Chemical Equation Presented) An efficient catalytic enantioselective preparation of synthetically useful pyranyl and piperidinyl allylic boronates was achieved via a palladium-catalyzed borylation/isomerization reaction on the corresponding alkenyl triflates. The influence of the base and solvent was found to be crucial on the regio- and enantioselectivity of this reaction. The overall borylation process constitutes a successful example of formal asymmetric isomerization of allylic ether/amine. The resulting allylic boronate reagents add to various aldehydes in a one-pot process to give synthetically useful alpha-hydroxyalkyl derivatives in high stereoselectivity.
- Lessard, Stephanie,Peng, Feng,Hall, Dennis G.
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supporting information; experimental part
p. 9612 - 9613
(2011/03/20)
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- NOVEL HETEROCYCLIC COMPOUNDS AND USES THEROF
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New substituted heterocyclic compounds, compositions containing them, and methods of using them for the inhibition of Raf kinase activity are provided. The new compounds and compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.
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- POLYCYCLIC INDAZOLE DERIVATIVES AND THEIR USE AS ERK INHIBITORS FOR THE TREATMENT OF CANCER
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Disclosed are the ERK inhibitors of formula 1.0: (Chemical formula should be inserted here as it appears on abstract in paper form) and the pharmaceutically acceptable salts, esters and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of formula 1.0.
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- SUBSTITUTED IMIDAZOHETEROCYCLES
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The present invention provides substituted imidazoheterocyclic compounds having the structure of formula I Also provided are pharmaceutically acceptable salts, acid salts, hydrates, solvates and stereoisomers of the compounds of formula I. The compounds are useful as modulators of cannabinoid receptors and for the prophylaxis and treatment of cannabinoid receptor-associated diseases and conditions, such as pain, inflammation and pruritis.
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Page/Page column 65
(2009/01/24)
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- Synthesis of alkenylboronates via palladium-catalyzed borylation of alkenyl triflates (or Iodides) with pinacolborane
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Various alkenyl iodides and triflates were borylated with pinacolborane in the presence of Et3N and a catalytic amount of PdCl2(dppf) and AsPh3 to afford the corresponding alkenylboronates in good yields.
- Murata, Miki,Oyama, Takashi,Watanabe, Shinji,Masuda, Yuzuru
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p. 778 - 780
(2007/10/03)
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