169750-31-6

Basic information

• Product Name: 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid
• Synonyms: 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid
• CAS NO: 169750-31-6
• Molecular Formula: C13H14F3NO2
• Molecular Weight: 273.25
• Mol File: 169750-31-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 340.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.343±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.30±0.40(Predicted)
• CAS DataBase Reference: 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid(169750-31-6)
• EPA Substance Registry System: 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid(169750-31-6)

Safety Data

• Hazardous Substances Data: 169750-31-6(Hazardous Substances Data)

Usage

Molecular Weight

267.26 g/mol
The molecular weight is the mass of one mole of the compound, calculated by adding the atomic weights of all the atoms in the molecular formula.

Structure

Benzyl group and trifluoromethyl group attached to a pyrrolidine ring with a carboxylic acid functional group
The structure of the compound consists of a pyrrolidine ring (a five-membered ring with one nitrogen atom) with a benzyl group (a phenyl group attached to a methylene group) and a trifluoromethyl group (a methyl group with three fluorine atoms) attached to it, as well as a carboxylic acid group (a carbonyl group attached to a hydroxyl group).

Polarity

High polarity

Solubility

Soluble in organic solvents, may have low solubility in water
Due to its polar and nonpolar components, the compound is likely to dissolve in organic solvents such as ethanol, methanol, or dimethyl sulfoxide (DMSO). However, its solubility in water may be limited due to the presence of the nonpolar benzyl and trifluoromethyl groups.

Use in Pharmaceutical Synthesis

Building block for potential drug candidates
As a member of the pyrrolidine carboxylic acid family, this compound is commonly used as a building block in the synthesis of pharmaceutical compounds. Its unique structure and properties make it a valuable tool in the development of new drugs and medicinal agents.

Biological Activity

Potential for synthesis of biologically active compounds
The specific structure of 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid allows for the possibility of creating biologically active compounds when used in chemical synthesis. This makes it an important compound in the field of medicinal chemistry.

Upstream product

• 152188-51-7 ethyl (+/-)-(3R,4R)-1-benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylate 
• 217096-03-2 trans-1-benzyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester 
• 93102-05-7 N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine 

Downstream Products

• 184844-93-7 (3S,4S)-1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid 
• 184844-96-0 (3R,4R)-1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid 

Relevant articles and documents

Discovery of 1-{(3R,4R)-3-[({5-Chloro-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)methyl]-4-methoxypyrrolidin-1-yl}prop-2-en-1-one (PF-06459988), a Potent, WT Sparing, Irreversible Inhibitor of T790M-Containing EGFR Mutants

First generation EGFR TKIs (gefitinib, erlotinib) provide significant clinical benefit for NSCLC cancer patients with oncogenic EGFR mutations. Ultimately, these patients' disease progresses, often driven by a second-site mutation in the EGFR kinase domain (T790M). Another liability of the first generation drugs is severe adverse events driven by inhibition of WT EGFR. As such, our goal was to develop a highly potent irreversible inhibitor with the largest selectivity ratio between the drug-resistant double mutants (L858R/T790M, Del/T790M) and WT EGFR. A unique approach to develop covalent inhibitors, optimization of reversible binding affinity, served as a cornerstone of this effort. PF-06459988 was discovered as a novel, third generation irreversible inhibitor, which demonstrates (i) high potency and specificity to the T790M-containing double mutant EGFRs, (ii) minimal intrinsic chemical reactivity of the electrophilic warhead, (iii) greatly reduced proteome reactivity relative to earlier irreversible EGFR inhibitors, and (iv) minimal activity against WT EGFR.

Synthesis and structure-activity relationships of 2-pyridones: II. 8- (fluoro-substituted pyrrolidinyl)-2-pyridones as antibacterial agents

The 8-position side chain of 2-pyridones is believed to be involved in the binding with bacterial DNA gyrase to form the ternary complex, making them very important for the activity of 2-pyridones. A series of 2-pyridones having fluoro-substituted amines at the 8-position has been synthesized and their antibacterial activities and parmacokinetic properties are reported.