848074-36-2

Usage

Physical state

Colorless liquid

Reactivity

Highly reactive

Sensitivity

Sensitive to air and moisture

Usage

Commonly used as a reagent in organic synthesis

Application

Particularly in the production of pharmaceuticals and other fine chemicals

Functional group introduction

Often used in reactions that involve the introduction of a trifluoromethyl functional group into organic molecules

Safety precautions

Should be handled with caution due to potential irritant and corrosive effects on the skin, eyes, and respiratory system

Upstream product

• 277756-46-4 1-(trifluoromethyl)cyclopropanecarboxylic acid 

Downstream Products

• 1395492-90-6 4-bromo-2-[1-(trifluoromethyl)cyclopropyl]pyridine 

Relevant academic research and scientific papers

Fluorinated Sulfinates as Source of Alkyl Radicals in the Photo-Enantiocontrolled β-Functionalization of Enals

The generation of sulfonyl radicals has long been known as a flexible strategy in a wide range of different sulfonylative transformations. Meanwhile their use in alkylation processes has been somehow limited due to their inherent difficulty in evolving to less-stable radicals after sulfur dioxide extrusion. Herein we report a convenient strategy that involves gem-difluorinated sulfinates as an “upgrading-mask”, allowing these precursors to decompose into their corresponding alkyl radicals. The electron–donor character of sulfinates in the formation of an electron donor–acceptor (EDA) complex with transient iminium ions is displayed, achieving the first example of a stereocontrolled light-driven insertion of gem-difluoro derivatives into unsaturated aldehydes. This methodology is compatible with flow conditions, maintaining identical levels of enantiocontrol.

Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis

Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.

SUBSTITUTED [1,2,4]TRIAZOLE COMPOUNDS AS FUNGICIDES

The present invention relates to substituted [1,2,4]triazole compounds of formula I and the N-oxides and the salts thereof, to the use of said compounds and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates to processes for preparing these compounds and to compositions comprising at least one compound I.

Discovery of β-Arrestin Biased, Orally Bioavailable, and CNS Penetrant Neurotensin Receptor 1 (NTR1) Allosteric Modulators

Neurotensin receptor 1 (NTR1) is a G protein coupled receptor that is widely expressed throughout the central nervous system where it acts as a neuromodulator. Neurotensin receptors have been implicated in a wide variety of CNS disorders, but despite extensive efforts to develop small molecule ligands there are few reports of such compounds. Herein we describe the optimization of a quinazoline based lead to give 18 (SBI-553), a potent and brain penetrant NTR1 allosteric modulator.

COMPOUNDS AND COMPOSITIONS AS RAF KINASE INHIBITORS

The present invention provides compounds of Formula (I) and (II) as described herein, and salts thereof, and therapeutic uses of these compounds for treatment of disorders associated with Raf kinase activity. The invention further provides pharmaceutical compositions comprising these compounds, and compositions comprising these compounds and a therapeutic co-agent.

SPIROCYCLIC COMPOUNDS

Disclosed herein are spirocyclic compounds, together with pharmaceutical compositions and methods of ameliorating and/or treating a cancer described herein with one or more of the compounds described herein.

FUSED MORPHOLINOPYRIMIDINES AND METHODS OF USE THEREOF

The present disclosure relates to Fused Morpholinopyrimidines, pharmaceutical compositions comprising an effective amount of a Fused Morpholinopyrimidine and methods for using a Fused Morpholinopyrimidine in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of a Fused Morpholinopyrimidine.

Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation

A simple method to convert readily available carboxylic acids into sulfinate salts by employing an interrupted Barton decarboxylation reaction is reported. A medicinally oriented panel of ten new sulfinate reagents was created using this method, including a key trifluoromethylcyclopropanation reagent, TFCS-Na. The reactivity of six of these salts towards C-H functionalization was field-tested using several different classes of heterocycles.

PROCESS FOR THE PREPARATION OF PROLINE DERIVATIVES

The present invention relates in part to a process for the preparation of a proline derivative of formula I wherein, R1 is C1-7-alkyl or wherein R4 is selected from the group consisting of C1-7-alkyl, halogen-C1-7-alkyl and phenyl optionally substituted by halogen; R2 is halogen or halogen-C1-7-alkyl; and R3 is selected from the group consisting of hydrogen, halogen, halogen-C1-7-alkyl, C1-7-alkoxy, halogen-C1-7-alkoxy and a 5- or 6-membered heterocyclic ring containing one or two nitrogen atoms, said ring being optionally substituted by C1-7-alkyl or halogen. The proline derivatives of the formula I are preferential inhibitors of the cysteine protease Cathepsin S and are therefore useful to treat metabolic diseases like diabetes, atherosclerosis, abdominal aortic aneurysm, peripheral arterial disease and diabetic nephropathy.

PROCESS FOR THE PREPARATION OF 1-ACYL-4-PHENYLSULFONYLPROLINAMIDE DERIVATIVES AND NEW INTERMEDIATES

A novel process for the preparation of proline derivatives of formula (I) wherein,R1 is selected from C1-7-alkyl or from formula (II) wherein R4 is selected from C1-7-alkyl, halogen-C1-7-alkyl or from phenyl which is optionally substituted by halogen; R2 is selected from halogen or halogen-C1-7-alkyl; and R3 is selected from hydrogen, halogen, halogen-C1-7-alkyl, C1-7-alkoxy, halogen-C1-7-alkoxy or from a 5- or 6-membered heterocyclic ring containing one or two nitrogen atoms, the ring which is optionally substituted by C1-7-alkyl or halogen is described. The proline derivatives of the formula I are preferential inhibitors of the cysteine protease Cathepsin S and are therefore useful to treat metabolic diseases like diabetes, atherosclerosis, abdominal aortic aneurysm, peripheral arterial disease and diabetic nephropathy.