13412-12-9

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-METHYLAMINOCROTONATE is used as a chemical intermediate for the synthesis of amlodipine analogues, specifically those bearing a short amino polyethylene glycol chain. This application is crucial for the development of new medications with potential improved properties, such as enhanced solubility, stability, or bioavailability, which can contribute to more effective treatments for various cardiovascular conditions.

InChI:InChI=1/C6H11NO2/c1-5(7-2)4-6(8)9-3/h4H2,1-3H3/b7-5+

Upstream product

• 4091-39-8 3-chloro-2-butanone 
• 105-45-3 acetoacetic acid methyl ester 
• 74-89-5 methylamine 
• 41607-86-7 β-Azidoisovaleriansaeuremethylester 
• 624-90-8 methyl azide 
• 623-43-8 methyl crotonate 
• 622-29-7 N-Benzylidenemethylamine 
• 17041-60-0 dimethyl ethylidenemalonate 

Downstream Products

• 54317-79-2 3-methyl-5-(1-methylamino-ethylidene)-[1,3]oxazinane-2,4,6-trione 
• 117648-80-3 1,2-Dimethyl-4-phenyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 117648-81-4 4-(3,4-Dimethoxy-phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 117648-83-6 4-(4,5-Dimethoxy-2-nitro-phenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 132368-65-1 3-Ethyl 1-methyl 4-hydroxy-2-methyl-6-oxo-4-(trifluoromethyl)cyclohexane-1,3-dicarboxylate 
• 132368-60-6 3-Ethyl 5-methyl 1,2,3,4-tetrahydro-2-hydroxy-1,4,6-trimethyl-2-(trifluoromethyl)-3,5-pyridinedicarboxylate 
• 109329-68-2 dimethyl 4-(2-chlorophenyl)-1,2,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 109329-69-3 2-(2-Chloro-phenyl)-4-methyl-6-methylamino-cyclohexa-3,5-diene-1,3-dicarboxylic acid dimethyl ester 
• 110520-09-7 2,5-Dimethyl-3-methoxycarbonyl-N-methyl-4-(4-amino-3-nitrophenyl)pyrrole 
• 30131-45-4 dimethyl 1,2,6-trimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 127896-40-6 4-(o-difluoromethoxyphenyl)-3,5-dimethoxycarbonyl-1,2,6-trimethyl-1,4-dihydropyridine 
• 107563-19-9 1,2,6-Trimethyl-4-(2-nitro-phenyl)-5-(2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 
• 107582-69-4 1,2,6-Trimethyl-5-(2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 
• 107563-20-2 4-(2-Difluoromethoxy-phenyl)-1,2,6-trimethyl-5-(2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

New Route to Functionalized Cyclohexenes in Solvent-free Conditions from Enamino Ketones and β-Oxo Alkenes

Enamino ketones 5 react with β-oxo alkenes 4, without solvent, at room temperature or under focused microwaves to give new, highly functionalized cyclohexenes 7 and 9 in good yields. A mechanism is proposed. The procedure is mild, efficient, economical and environmentally benign. - Keywords: solvent-free reactions; enamino ketones; cyclohexenes; β-oxo alkenes

Synthesis of Spiro-Δ2-Pyrrolin-4-One Pseudo Enantiomers via an Organocatalyzed Sulfa-Michael/Aldol Domino Sequence

Δ2-Pyrrolin-4-ones undergo organocatalyzed sulfa-Michael/aldol domino spirocyclizations with mercaptoacetaldehyde dimer. The products contain three contiguous stereocenters (ee up to 99%, dr up to 95:5, 25 examples) and can be transformed into analogues of natural products. With the use of a single catalyst, the absolute configuration of the products were determined by the configuration of the exocyclic double bond of the starting material. These results point at the possibility of a widespread use of unsaturated Δ2-pyrrolin-4-ones in various (organo)catalyzed (cascade) transformations for accessing libraries of 3D-rich pyrrolone-based (spiro)heterocycles. (Figure presented.).

Design of a graphene oxide-SnO2 nanocomposite with superior catalytic efficiency for the synthesis of β-enaminones and β-enaminoesters

A graphene oxide (GO)-SnO2-based nanocomposite was synthesized by decorating the graphene oxide surface with SnO2 nanoparticles via a solvothermal process. The nanocomposite was characterized using Fourier transform infrared spectra (FTIR), FT-Raman spectroscopy, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Field-emission Scanning electron microscopy (FE-SEM), Energy dispersive X-ray spectroscopy (EDS), Transmission electron microscopy (TEM) and N2 adsorption/desorption study. The FE-SEM and TEM images demonstrate the uniform distribution of the SnO2 nanoparticles on the GO surface and high-resolution transmission electron microscopy (HRTEM) confirms an average particle size of 8-12 nm. The GO-SnO2 nanocomposite has been found to be an extremely efficient catalyst for the synthesis of β-enaminones and β-enaminoesters in methanol solvent and also, in solventless conditions. The GO-SnO2 nanocomposites exhibited synergistically more superior catalytic efficiency compared to pure graphene oxide and SnO2 nanoparticles. The reaction conditions were optimized by changing different parameters such as catalyst, solvent, catalyst loading, and temperature. It has been found that the catalyst gave higher activity under solventless conditions than methanol. The GO-SnO2 composite was recycled for up to four cycles with minimal loss in activity.

Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence

A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialkyl-8-carbomethoxy-1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a β-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50-86% yields when R 1 is n-alkyl but ≤30% yields when R1 is α-branched.

Bexarotene prodrugs: Targeting through cleavage by NQO1 (DT-diaphorase)

Bexarotene, a retinoid X receptor (RXR) agonist, is being tested as a potential disease modifying treatment for neurodegenerative conditions. To limit the peripheral exposure of bexarotene and release it only in the affected areas of the brain, we designe

LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.

FUNGICIDAL PYRAZOLES

Disclosed are compounds of Formula (1) and Formula (1A) including all stereoisomers, N oxides, and salts thereof,wherein Q1, Q2, R1, R2, R4, R5 and X are as defined in the disclosure. Also

POLYCYCLIC LPA1 ANTAGONIST AND USES THEREOF

Described herein is the LPA1 antagonist 1- {4'-[3-methyl-4-((R)- l-phenyl-ethoxycarbonylamino)- isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid (Compound 1), or pharmaceutically acceptable salts thereof. Also described are methods of preparing t

Cu(OAc)2/TFA-promoted formal [3 + 3] cycloaddition/oxidation of enamines and enones for synthesis of multisubstituted aromatic amines

New strategies for the oxidative cycloaddition of enones with enamines are developed. These cycloaddition reactions directly afford substituted aromatic amines, which are important in organic chemistry, in moderate to good yield. Cu(OAc)2/TFA is shown to be essential to achieve high reaction efficiency.

LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in com