184844-96-0

Basic information

• Product Name: (3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid
• Synonyms: (3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid
• CAS NO: 184844-96-0
• Molecular Formula: C₁₃H₁₄F₃NO₂
• Molecular Weight: 273.25
• Mol File: 184844-96-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 92℃(dec)
• Appearance: /
• CAS DataBase Reference: (3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid(184844-96-0)
• EPA Substance Registry System: (3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid(184844-96-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 184844-96-0(Hazardous Substances Data)

Usage

General Description

The chemical (3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid is a compound with a complex molecular structure. It contains a tetrahydro-1H-pyrrole ring, a benzyl group, and a trifluoromethyl group, as well as a carboxylic acid functional group. The molecule has a chiral center, with a 3R configuration. (3R,4R)-1-Benzyl-4-(trifluoromethyl)tetrahydro-1H-pyrrole-3-carboxylic acid may have potential applications in pharmaceutical research, particularly in the development of new drugs or as a building block for the synthesis of other compounds. Its specific properties and potential uses would likely depend on further studies and experiments.

Upstream product

• 217096-03-2 trans-1-benzyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester 
• 152188-51-7 ethyl (+/-)-(3R,4R)-1-benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylate 
• 169750-31-6 (3S,4S)-1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid 
• 93102-05-7 N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine 

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.