20485-39-6

Usage

Uses

Ethyl 4-methyl-1,3-oxazole-5-carboxylate is used as a chemical intermediate in the synthesis of various compounds. Its unique structure with both polar and nonpolar regions allows it to be a versatile building block in the development of new materials and pharmaceuticals.
Used in Pharmaceutical Industry:
Ethyl 4-methyl-1,3-oxazole-5-carboxylate is used as a key intermediate for the synthesis of pharmaceutical compounds. Its structural features enable the creation of new drug molecules with potential therapeutic applications.
Used in Chemical Industry:
Ethyl 4-methyl-1,3-oxazole-5-carboxylate is used as a precursor in the production of specialty chemicals. Its reactivity and structural properties make it a valuable component in the synthesis of advanced materials with specific properties for various applications.

InChI:InChI=1/C7H9NO3/c1-3-10-7(9)6-5(2)8-4-11-6/h4H,3H2,1-2H3

Upstream product

• 64-18-6 formic acid 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 77287-34-4 formamide 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 141-97-9 ethyl acetoacetate 
• 584-08-7 potassium carbonate 
• 16712-16-6 ammonium formate 

Downstream Products

• 4866-00-6 4-methyl oxazole-5-carboxamide 
• 45515-23-9 5-hydroxymethyl-4-methyloxazole 
• 2510-32-9 4-methyl-1,3-oxazole-5-carboxylic acid 
• 45515-22-8 4-methyl-5-oxazolylmethyl chloride 
• 863679-31-6 3-[(3-chloropropyl)sulfanyl]-4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-4H-1,2,4-triazole 
• 933782-12-8 2-cyclohexyl-4-ethoxycarbonyl-4-methyl-1,3-oxazole 
• 1387556-68-4 ethyl 2-(5-(ethoxycarbonyl)-4-methylthiazol-2-yl)-4-methyloxazole-5-carboxylate 
• 3944-31-8 diethyl 4,4?-dimethyl-2,2?-bithiazole-5,5?-dicarboxylate 
• 1403502-53-3 ethyl 4-methyl-2-p-tolyloxazole-5-carboxylate 
• 1003-52-7 5-cyano-4-methyl-oxazole 
• 106166-54-5 4-methyl-5-(4-phenyl-thiazol-2-yl)-oxazole 
• 62348-24-7 4-Methyl-5-oxazolecarbonyl chloride 
• 911297-49-9 6-[2-(4-methyl-oxazole-5-carbonyl)-phenyl]-hept-2-en-4-ynoic acid ethyl ester 
• 911297-36-4 (4-methyl-oxazol-5-yl)-[2-(1-methyl-3-trimethylsilanyl-prop-2-ynyl)-phenyl]methanone 

Relevant academic research and scientific papers

Synthesis of oxazolyl- and furanyl-substituted imidazole hydrochlorides and methiodides

Oxazolyl-5- and furanyl-2-substituted imidazoles have been synthesized by coupling the two ring systems via the dipolar cycloadditon of tosyl methyl isocyanide to the corresponding oxazolyl and furanyl aldimines in basic media. These substitute oxazolyl and furanylimidazole bases obtained in this manner were then subjected to hydrogen chloride gas and to methyl iodide to form the corresponding hydrochlorides and methyliodides, respectively. All compounds were purified, characterized and then tested for muscarinic binding affinity. Biological test results revealed low muscarinic receptor affinity and selectivity.

Synthesis of oxazolyl-substituted morpholinium salts

Morpholinium salts coupled to oxazolyl moieties have been synthesized via nucleophilic substitution of a series of oxazolyl chlorides with morpholine. The oxazole moieties were first synthesized and then coupled with morpholine. The corresponding hydrochloride and methyl iodide salts were obtained, purified, characterized and then tested for muscarinic receptor binding affinity. Biological test results from MDS Pharma Services revealed no significant muscarinic receptor affinity.

Optimization of Triarylpyridinone Inhibitors of the Main Protease of SARS-CoV-2 to Low-Nanomolar Antiviral Potency

Non-covalent inhibitors of the main protease (Mpro) of SARS-CoV-2 having a pyridinone core were previously reported with IC50 values as low as 0.018 μM for inhibition of enzymatic activity and EC50 values as low as 0.8 μM for inhibition of viral replication in Vero E6 cells. The series has now been further advanced by consideration of placement of substituted five-membered-ring heterocycles in the S4 pocket of Mpro and N-methylation of a uracil ring. Free energy perturbation calculations provided guidance on the choice of the heterocycles, and protein crystallography confirmed the desired S4 placement. Here we report inhibitors with EC50 values as low as 0.080 μM, while remdesivir yields values of 0.5-2 μM in side-by-side testing with infectious SARS-CoV-2. A key factor in the improvement is enhanced cell permeability, as reflected in PAMPA measurements. Compounds 19 and 21 are particularly promising as potential therapies for COVID-19, featuring IC50 values of 0.044-0.061 μM, EC50 values of ca. 0.1 μM, good aqueous solubility, and no cytotoxicity.

3-(AZOLYLMETHOXY)BIPHENYL DERIVATIVES AS INHIBITORS OF THE PD-1/PD-L1 PROTEIN/PROTEIN INTERACTION

The present invention provides novel compounds of formula (I) that are useful as inhibitors of the PD-1/PD-L1 protein/protein interaction. The compounds may be used in the treatment of cancer, infectious diseases and neurodegenerative diseases such as schizophrenia, Alzheimer, multiple sclerosis or Parkinson.

Widely Exploited, Yet Unreported: Regiocontrolled Synthesis and the Suzuki–Miyaura Reactions of Bromooxazole Building Blocks

An approach to synthesis of 2-, 4-, and 5-bromooxazoles is described. The method was optimized, and its scope was extended to all three isomeric parents, as well as various alkyl- and aryl-substituted bromooxazoles. It was found that direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common for all substrates and led exclusively to the target substituted 2-, 4- and 5-bromooxazoles on multigram scale. The utility of the multipurpose building blocks obtained in this work was demonstrated in the Suzuki–Miyaura cross-coupling reaction under parallel synthesis conditions.

NEW INTERMEDIATE COMPOUND FOR PREPARING VITAMIN B6

Provided is a new intermediate compound for preparing vitamin B6, which can be used to synthesize the known intermediate compound for preparing vitamin B6, 4-methyloxazole-5-carboxyLate. Further provided is a process for preparing the new intermediate compound and a process for preparing the known intermediate compound 4-methyloxazole-5-carboxylate from the new intermediate compound.

A NEW PROCESS FOR PREPARATION OF 4-METHYLOXAZOLE-5-CARBOXYLIC ESTER

The present invention is related to a new process for the preparation of 4-methyloxazole-5-carboxylic ester, which is a valuable intermediate in the synthesis of pyridoxine (vitamin B6). The present invention is also related to a new intermediate for the preparation of 4-methyloxazole-5-carboxylic ester and processes for the preparation thereof.

Method for synthesizing furanosteroids

The present invention is a method for synthesizing furanosteroids. The method involves intramolecular Diels-Alder/retro-Diels-Alder reaction and tautomerization of a functionalized alkyne oxazole to produce a furo[2,3-b]phenol derivative which is elaborated by intermolecular and intramolecular condensations to generate ring-A of the furanosteroid. Furanosteroids and pharmaceutical compositions containing the same are also provided.

PYRAZOLE COMPOUNDS AND USE THEREOF

The pyrazole compound of the present invention is represented by the following general formula (I). The pyrazole compound of the present invention or a salt thereof or a solvate thereof potently inhibits liver glycogen phosphorylase, and, therefore, is useful as a therapeutic or prophylactic agent for diabetes. wherein each symbol denotes as described in the specifications.

Synthesis of furanyl and oxazolyl N-substituted piperidine and imidazoline salts as potential agonists of M1 muscarinic receptors

(Chemical Equation Presented) Furanyl and oxazolyl N-substituted imidazoline salts were prepared by reacting furanyl and oxazolyl esters with ethylenediamine and trimethyl aluminum, followed by the addition of methyl iodide or hydrogen chloride. The piperidinium salts were prepared by treating furanyl and oxazolyl chlorides with piperidine base, followed by the addition of methyl iodide or hydrogen chloride.