106877-20-7

Usage

Uses

Used in Organic Synthesis:
3-Methoxy-4-(trifluoromethyl)phenylamine is used as a building block in organic synthesis for the creation of a variety of biologically active molecules. Its unique structure allows for the development of new compounds with potential applications in various fields.
Used in Pharmaceutical Research:
In pharmaceutical research, 3-Methoxy-4-(trifluoromethyl)phenylamine is utilized as a key intermediate for the synthesis of pharmaceuticals. Its incorporation into drug molecules can enhance their efficacy and selectivity, contributing to the advancement of novel therapeutic agents.
Used in Agrochemical Production:
3-Methoxy-4-(trifluoromethyl)phenylamine is used as an intermediate in the production of agrochemicals. Its role in this industry is crucial for the development of effective pesticides and other agricultural chemicals that protect crops and enhance yield.
Used in Dye Manufacturing:
3-Methoxy-4-(trifluoromethyl)phenylamine is also employed in the manufacturing of dyes, where it contributes to the creation of colorants with specific properties. Its use in this application is indicative of its versatility and the breadth of its potential impact on various commercial products.

InChI:InChI=1S/C8H8F3NO/c1-13-7-4-5(12)2-3-6(7)8(9,10)11/h2-4H,12H2,1H3

Upstream product

• 75-63-8 Bromotrifluoromethane 
• 536-90-3 m-Anisidine 
• 453560-74-2 2-methoxy-4-nitro-1-(trifluoromethyl)benzene 
• 2597-56-0 4-nitro-o-anisic acid 
• 887144-94-7 Togni's reagent II 
• 5458-84-4 2-iodo-5-nitroanisole 
• 276861-63-3 3-methoxy-4-(trifluoromethyl)benzoic acid 

Downstream Products

• 694514-19-7 2-bromo-5-methoxy-4-(trifluoromethyl)aniline 
• 1257832-39-5 N-[4-[8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-6-(trifluoromethyl)-3-quinolyl]phenyl]methanesulfonamide 
• 1257832-33-9 N-[4-[8-bromo-5-methoxy-6-(trifluoromethyl)-3-quinolyl]phenyl]methanesulfonamide 
• 1485749-11-8 tert-butyl N-[3-[4-(methanesulfonamido)phenyl]-5-methoxy-6-(trifluoromethyl)-8-quinolyl]carbamate 
• 1485749-14-1 N-[4-[8-amino-5-methoxy-6-(trifluoromethyl)-3-quinolyl]phenyl]methanesulfonamide 

Relevant academic research and scientific papers

Deoxofluorination of (Hetero)aromatic Acids

Diverse trifluoromethyl-substituted compounds were synthesized by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids with sulfur tetrafluoride. The obtained products were used as starting materials in the preparation of novel fluorinated amino acids, anilines, and aliphatic amines - valuable building blocks for medicinal chemistry and agrochemistry.

Chagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series

Acylaminobenzothiazole hits were identified as potential inhibitors of Trypanosoma cruzi replication, a parasite responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure-activity relationship, allowing optimization of antiparasite activity, physicochemical parameters, and ADME properties. We identified compound 50 as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079 μM) and an enhanced metabolic stability (human clearance = 0.41 mL/min/g) and opportunity for the oral route of administration. After tolerability assessment, 50 demonstrated a promising in vivo efficacy.

Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni's Reagent

An efficient nickel-catalyzed C-H trifluoromethylation for the synthesis of trifluoromethylated free anilines using Togni's reagent has been developed. This approach exhibits a good functional group tolerance, good regioselectivity, and chemoselectivity under mild conditions. The newly developed economical one-step method is a better alternative to synthesize trifluoromethylated free anilines.

Preparation method of trifluoromethylamine

The invention relates to a preparation method of trifluoromethylamine. The method includes the following steps that aromatic amine shown in the formula (1) and a trifluoromethyl reagent shown in the formula (2) react in a solvent under the condition that an alkali and/or nickel compound exists, and the trifluoromethylamine compound shown in the formula (3) is generated. According to the preparation method of trifluoromethylamine, aromatic amine and 1-trifluoromethyl-1,2-iodobenzoyl-3(H)-ketone serve as raw materials and react under the condition that the alkali and/or nickel compound exists through the amino positioning effect on aromatic nucleus. The synthesis steps of the method are simple, the cost of the raw materials is low, the production cost of trifluoromethylamine can be greatly reduced, and large-scale industrialized production is promoted.

NOVEL 6-6 BICYCLIC AROMATIC RING SUBSTITUTED NUCLEOSIDE ANALOGUES FOR USE AS PRMT5 INHIBITORS

The present invention relates novel 6-6 bicyclic aromatic ring substituted nucleoside analogues of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PRMT5 inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

Discovery of N-[4-[6-tert-butyl-5-methoxy-8-(6-methoxy-2-oxo-1 H -pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide (RG7109), a potent inhibitor of the hepatitis C virus NS5B polymerase

In the past few years, there have been many advances in the efforts to cure patients with hepatitis C virus (HCV). The ultimate goal of these efforts is to develop a combination therapy consisting of only direct-antiviral agents (DAAs). In this paper, we

HETEROCYCLIC ANTIVIRAL COMPOUNDS

Compounds having the formula I wherein wherein R1, R2, R3, R4, X1, X2, X3 and X4 and as defined herein are Hepatitis C virus NS5b polymerase inhibitors. Also disclosed are compositions and methods for treating an HCV infection and inhibiting HCV replication.

DIHYDROPYRIDONE UREAS AS P2X7 MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R1, R2, R3, R4 and R5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

Reactions of Trifluoromethyl Bromide and Related Halides: Part 10. Perfluoroalkylation of Aromatic Compounds induced by Sulphur Dioxide Radical Anion Precursors

Perfluoroalkylation of electron-rich aromatic compounds with trifluoromethyl bromide, or long-chain perfluoroalkyl iodides, was performed in the presence of sodium dithionite or zinc-sulphur dioxide.This alkylation occurred at the ortho and para positions relative to the amino or hydroxy substitutent.Pyrroles were perfluoroalkylated regioselectively at the 2-position.This alkylation was interpreted as a radical aromatic substitution; the formation of the perfluoroalkyl radical can be induced by a single-electron transfer from sulphur dioxide radical anion to the perfluoroalkyl halide.

Perfluoroalkylation of Anilines in the Presence of Zinc and Sulphur Dioxide

Arylamines are transformed into their ortho- and para-trifluoromethyl derivatives by the action of trifluoromethyl bromide under slight pressure in the presence of 0.15 equiv. of zinc and sulphur dioxide in dimethylformamide.