55107-14-7

Usage

Uses

Used in Chemical Synthesis:
Methyl pivaloylacetate is used as a substrate in InCl3-catalyzed syntheses for the production of new dibenzo(d,f)(1,3)dioxepines and 12H-dibenzo(d,g)(1,3)dioxocin derivatives. Its unique structure allows for the formation of these complex organic compounds, which have potential applications in various fields, such as pharmaceuticals and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl pivaloylacetate is used as a key intermediate in the synthesis of various drugs and drug candidates. Its reactivity and compatibility with different reaction conditions make it a valuable component in the development of new medications.
Used in Materials Science:
Methyl pivaloylacetate is also utilized in the preparation of neat α-oxoketene, carbomethoxypivaloylketene, and other advanced materials. These materials have potential applications in areas such as polymer science, coatings, and adhesives, where their unique properties can be harnessed for improved performance and functionality.

InChI:InChI=1/C8H14O3/c1-8(2,3)6(9)5-7(10)11-4/h5H2,1-4H3

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 42957-17-5 methyl 5,5-dimethyl-2,4-dioxohexanoate 
• 3282-30-2 pivaloyl chloride 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 7065-46-5 3,3-dimethylbutanoic acid chloride 
• 144864-97-1 methyl tert-butyl(pivaloyl)acetate 
• 108-59-8 malonic acid dimethyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 4195-19-1 pivaloyl imidazole 
• 67-56-1 methanol 
• 2033-24-1 cycl-isopropylidene malonate 
• 75-98-9 Trimethylacetic acid 
• 13547-70-1 1-chloro-3,3-dimethyl-butan-2-one 
• 201230-82-2 carbon monoxide 

Downstream Products

• 66698-66-6 6-tert-butyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one 
• 77747-43-4 6-tert-Butyl-2-ureido-4(3H)-pyrimidinone 
• 107403-12-3 3-hydroxy-5-tert-butylisoxazole 
• 75914-61-3 3-(tert-butyl)isoxazol-5 (4H)-one 
• 177847-16-4 methyl 2-(4-bromophenylacetyl)-3-tert-butyl-3-oxopropanoate 
• 185420-79-5 2-(2-Methoxycarbonyl-1-methoxycarbonylmethyl-ethyl)-4,4-dimethyl-3-oxo-pentanoic acid methyl ester 
• 150943-32-1 (+/-)-methyl 3-hydroxy-4,4-dimethylpentanoate 
• 665006-08-6 4-(methoxycarbonyl)-7,7-dimethyl-1-phenyl-3,6-octanedione 
• 79606-79-4 2-(Hydroxy-phenyl-methyl)-5,5-dimethyl-4-oxo-hexanoic acid methyl ester 
• 124645-64-3 methyl 2-(1-oxo-1-phenyl-methyl)-5,5-dimethyl-4-oxo-hexanoate 
• 875918-15-3 1-[o-(trifluoromethyl)phenyl]-2-(methoxycarbonyl)-5,5-dimethyl-1,4-hexanedione 
• 665006-37-1 1-(p-chlorophenyl)-2-(methoxycarbonyl)-5,5-dimethyl-1,4-hexanedione 
• 1047641-71-3 4,4-dimethyl-3-oxo-pentanoic acid [2-(2,4-dichloro-phenoxy)-ethyl]-amide 
• 75-98-9 Trimethylacetic acid 

Relevant academic research and scientific papers

The discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine cannabinoid type 2 receptor agonist

The development of selective CB2 receptor agonists is a promising therapeutic approach for the treatment of inflammatory diseases, without CB1 receptor mediated psychoactive side effects. Preliminary structure-activity relationship studies on pyrazoylidene benzamide agonists revealed the -ylidene benzamide moiety was crucial for functional activity at the CB2 receptor. A small library of compounds with varying linkage moieties between the pyrazole and substituted phenyl group has culminated in the discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine agonist 19 (CB2R EC50 = 19 nM, CB1R EC50 > 10 μM). Docking studies have revealed key structural features of the linkage group that are important for potent functional activity.

Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).

Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis

Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.

Chiral Vanadyl(V) Complexes Enable Efficient Asymmetric Reduction of β-Ketoamides: Application toward (S)-Duloxetine

High-valent chiral oxidovanadium(V) complexes derived from 3,5-substituted-N-salicylidene-l-tert-leucine were used as catalysts in asymmetric reduction of N-benzyl-β-ketoamides. Among six different solvents, three different alcohol additives, and two different boranes examined, the use of pinacolborane in tetrahydrofuran (THF) with a t-BuOH additive led to the best results at -20 °C. The corresponding β-hydroxyamides can be furnished with yields up to 92percent and an enantiomeric excess (ee) up to 99percent. We have successfully extended this catalytic protocol for the synthesis of an (S)-duloxetine precursor.

Preparation method of 4, 4-dimethyl-3-oxo-methyl pentanoate

The invention discloses a preparation method of 4, 4-dimethyl-3-oxo-methyl pentanoate. The method includes: taking pinacolone, sodium hydrogen and dimethyl carbonate as the raw materials, and using toluene as the solvent, carrying out stirring reaction at 55-60DEG C, then performing cooling, and at a pH of 4-5, preparing a 4, 4-dimethyl-3-oxo-methyl pentanoate crude product; and subjecting the 4, 4-dimethyl-3-oxo-methyl pentanoate crude product to distillation under the conditions of a vacuum degree of less than 10mm Hg and a temperature of 90-95DEG C. By means of the method provided by the invention, the 4, 4-dimethyl-3-oxo-methyl pentanoate has high distillation yield, the product purity is high, the main content is up to more than 98%, and the total yield is up to 96%.

Direct oxidative coupling of enamines and electron-deficient amines: TBAI/TBHP-mediated synthesis of substituted diaminoalkenes under metal-free conditions

A metal-free cross-coupling of enamines and electron-de fi cient amines through oxidative C(sp2)-N bond formation has been realized by using TBAI as catalyst and TBHP as oxidant. This novel strategy allows for an efficient organocatalytic synthesis of the synthetically useful diaminoalkene derivatives and is highlighted by appealing features such as readily available of the starting materials, wide substrate scope and transition-metal-free characteristics. (Chemical Equation Presented).

Diaryl- and triaryl-pyrrole derivatives: Inhibitors of the MDM2-p53 and MDMX-p53 protein-protein interactions

Screening identified 2-(3-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)- ylidene)methyl)-2,5-dimethyl-1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b] thiophene-3-carbonitrile as an MDM2-p53 inhibitor (IC50 = 12.3 μM). MDM2-p53 and MDMX-p53 activity was seen for 5-((1-(4-chlorophenyl)-2,5- diphenyl-1H-pyrrol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (MDM2 IC50 = 0.11 μM; MDMX IC50 = 4.2 μM) and 5-((1-(4-nitrophenyl)-2,5-diphenyl-1H-pyrrol-3-yl)methylene)pyrimidine-2,4,6(1H, 3H,5H)-trione (MDM2 IC50 = 0.15 μM; MDMX IC50 = 4.2 μM), and cellular activity consistent with p53 activation in MDM2 amplified cells. Further SAR studies demonstrated the requirement for the triarylpyrrole moiety for MDMX-p53 activity but not for MDM2-p53 inhibition. The Royal Society of Chemistry.

CHEMICAL COMPOUNDS

The invention is directed to to substituted indazole derivatives. Specifically, the invention is directed to compounds according to Formula I: wherein R1 - R6 and X are defined herein. The compounds of the invention are inhibitors of PDK1 and can be useful in the treatment of disorders characterized by constitutively activated ACG kinases such as cancer and more specifically leukemia and cancers of the breast, colon, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PDK1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Structure-activity relationship study of [1,2,3]thiadiazole necroptosis inhibitors

Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling non-regulated necrosis. This form of cell death can be induced in an array of cell types in apoptotic deficient conditions with death receptor family ligands. A series of [1,2,3]thiadiazole benzylamides was found to be potent necroptosis inhibitors (called necrostatins). A structure-activity relationship study revealed that small cyclic alkyl groups (i.e. cyclopropyl) and 2,6-dihalobenzylamides at the 4- and 5-positions of the [1,2,3]thiadiazole, respectively, were optimal. In addition, when a small alkyl group (i.e. methyl) was present on the benzylic position all the necroptosis inhibitory activity resided with the (S)-enantiomer. Finally, replacement of the [1,2,3]thiadiazole with a variety of thiophene derivatives was tolerated, although some erosion of potency was observed.

Carbonylation of alpha-chloroketones to beta-keto esters using palladium carbene catalysts

The present invention is a novel process for producing β-ketoesters 1 by contacting an α-chloroketone 2 with carbon monoxide and a hydroxyl-containing compound of formula R3OH in the presence of a base and a palladium carbene catalyst complex 3. The subject catalysts demonstrate superior rates and selectivity when compared to known (Ph3P)2PdCl2.