881673-98-9

Basic information

• Product Name: ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate
• Synonyms: ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate
• CAS NO: 881673-98-9
• Molecular Weight: 249.242
• Mol File: 881673-98-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate(881673-98-9)
• EPA Substance Registry System: ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate(881673-98-9)

Safety Data

• Hazardous Substances Data: 881673-98-9(Hazardous Substances Data)

Upstream product

• 445-27-2 2'-Fluoroacetophenone 
• 655-15-2 2-bromo-2'-fluoroacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 881677-02-7 5-(2-fluorophenyl)-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde 
• 881677-04-9 1-{[3-(ethylsulfonyl)phenyl]sulfonyl}-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde 
• 881677-06-1 2-{[2-(2-fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile 
• 881677-08-3 4-{[2-(2-fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile 
• 881677-09-4 5-(2-fluorophenyl)-1-[(2-fluorophenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde 
• 881677-11-8 5‐(2-fluorophenyl)‐1‐(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde 
• 881674-56-2 5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde 
• 881674-58-4 (5-(2-fluorophenyl)-1H-pyrrol-3-yl)methanol 
• 881674-06-2 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester 
• 881681-00-1 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine 
• 2098974-13-9 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrole-3-yl]-N-methylmethylamine fumaric acid salt 
• 881674-01-7 ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate 

Relevant articles and documents

Conformational Preference of 2′-Fluoro-Substituted Acetophenone Derivatives Revealed by Through-Space 1H-19F and 13C-19F Spin-Spin Couplings

The conformational properties of 2′-fluoro-substituted acetophenone derivatives were elucidated based on Hα-F and Cα-F through-space spin-spin couplings (TS-couplings), which occur between two atoms constrained at a distance smaller than the sum of their van der Waals radii. This study revealed that 2′-fluoro-substituted acetophenone derivatives in solutions form exclusively s-trans conformers by analyzing their NMR spectra focused on the TS-couplings. The magnitudes of the coupling constants 5J (Hα, F) and 4J (Cα, F) correlate linearly with the value of the dielectric constant of the solvents. Furthermore, s-trans conformations of the two derivatives were confirmed by X-ray crystallographic analysis. These conformational preferences were consistent with the DFT calculations. The s-cis conformer, in which fluorine and oxygen atoms lie in a syn-periplanar mode, may be subject to strong repulsion between the two polar atoms and become unstable. The s-trans preference of the 2′-fluoro-substituted acetophenone derivatives may be utilized in drug design.

Preparation method of drug for treating gastric acid related diseases

The invention discloses a preparation method of a drug TAK438 for treating gastric acid related diseases. According to the preparation method, 2-bromo-2'-fluoroacetophenone is taken as the primary raw material, and the target product TAK438 is obtained through the following reactions: condensation reaction, cyclization reaction, reduction reaction, sulfonylation reaction, and reductive amination reaction. The preparation method has the advantages of easily-available raw material, easy control, and high yield, and can be applied to industrial production.

Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3- ylsulfonyl)-1 H -pyrrol-3-yl]- n -methylmethanamine fumarate (tak-438) as a Potassium-Competitive Acid Blocker (P-CAB)

In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log"‰D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H +,K+-ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)- 1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.