149978-43-8

Basic information

• Product Name: 2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine
• Synonyms: 2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine;1-Methyl-3-(trifluoromethyl)-1h-pyrazol-5-amine;1H-Pyrazol-5-amine, 1-methyl-3-(trifluoromethyl)-
• CAS NO: 149978-43-8
• Molecular Formula: C5H6F3N3
• Molecular Weight: 165.1164496
• Mol File: 149978-43-8.mol

Chemical Properties

• Boiling Point: 227.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.50±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.21±0.10(Predicted)
• CAS DataBase Reference: 2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine(149978-43-8)
• EPA Substance Registry System: 2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine(149978-43-8)

Safety Data

• Hazardous Substances Data: 149978-43-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine is used as an intermediate in the synthesis of pharmaceuticals for its potential to contribute to the development of new drugs. Its unique structural features allow it to be a key component in creating novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine serves as an intermediate in the synthesis of agrochemicals, potentially enhancing the effectiveness of pesticides and other agricultural chemicals.
Used in Organic Chemistry:
2-Methyl-5-trifluoroMethyl-2H-pyrazol-3-ylaMine is utilized as a building block in organic chemistry reactions, facilitating the creation of new chemical entities for a range of applications beyond pharmaceuticals and agrochemicals. Its versatility in chemical reactions makes it a promising candidate for further exploration and development in the field of organic chemistry.

Upstream product

• 110234-68-9 3-cyano-1,1,1-trifluoroacetone 
• 302-15-8 methylhydrazine sulfuric acid 
• 154471-65-5 1-methyl-3-trifluoromethylpyrazol 
• 128694-63-3 1-methyl-3-(trifluoromethyl)pyrazole-5-carboxylic acid 
• 60-34-4 methylhydrazine 

Downstream Products

• 1453850-44-6 (S)-1-(1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl)-4-(2-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one 

Relevant articles and documents

Synthesis and Biological Activity of Novel Pyrazol-5-yl-benzamide Derivatives as Potential Succinate Dehydrogenase Inhibitors

To promote the discovery and development of new fungicides, a series of novel pyrazol-5-yl-benzamide derivatives were designed, synthesized by hopping and inversion of amide groups of pyrazole-4-carboxamides, and evaluated for their antifungal activities. The bioassay data revealed that compound 5IIc exhibited an excellent in vitro activity against Sclerotinia sclerotiorum with an EC50 value of 0.20 mg/L, close to that of commercial fungicide Fluxapyroxad (EC50 = 0.12 mg/L) and Boscalid (EC50 = 0.11 mg/L). For Valsa mali, compound 5IIc (EC50 = 3.68 mg/L) showed a significantly higher activity than Fluxapyroxad (EC50 = 12.67 mg/L) and Boscalid (EC50 = 14.83 mg/L). In addition, in vivo experiments proved that compound 5IIc has an excellent protective fungicidal activity with an inhibitory rate of 97.1% against S. sclerotiorum at 50 mg/L, while the positive control Fluxapyroxad showed a 98.6% inhibitory effect. The molecular docking simulation revealed that compound 5IIc interact with TRP173, SER39, and ARG43 of succinate dehydrogenase (SDH) through a hydrogen bond and p-πinteraction, which could explain the probable mechanism of the action between compound 5IIc and target protein. Also, the SDH enzymatic inhibition assay was carried out to further validate its mode of action. These results demonstrate that compound 5IIc could be a promising fungicide candidate and provide a valuable reference for further investigation.

Practical synthetic method for functionalized 1-methyl-3/5-(trifluoromethyl)-1H-pyrazoles

A new, high-yielding, and practical method for synthesis of 1-methyl-3-(trifluoromethyl)-1H-pyrazole and 1-methyl- 5-(trifluoromethyl)-1H-pyrazole, key intermediates for important building blocks relevant to medicinal and agrochemistry, is developed. A one-step procedure for synthesis of the regioisomeric mixture of target pyrazoles was proposed starting from 4-ethoxy- 1,1,1-trifluoro-3-buten-2-one. The procedure for separation of this mixture was elaborated on the basis of the boiling point vs pressure diagram analysis. The efficient synthetic strategies for regioisomeric building blocks bearing CF3 groups at the 3rd and 5th positions were demonstrated. A set of 1-methyl-3-(trifluoromethyl)-1H-pyrazoles containing such a functional group as aldehyde, acid, boron pinacolate, lithium sulfinate, and sulfonyl chloride was synthesized based on lithiation of 1-methyl-3-(trifluoromethyl)- 1H-pyrazole in a flow reactor. Bromination of both 1-methyl-3-(trifluoromethyl)-1H-pyrazole and 1-methyl-5-(trifluoromethyl)-1Hpyrazole by NBS in mild conditions was performed. The introduction of the functional group at the 4th position of 1-methyl-5- (trifluoromethyl)-1H-pyrazole was illustrated by the optimized synthesis of the corresponding aldehyde and acid based on the Br-Li exchange in an appropriate bromide. Alternatively, the introduction of the functional group (acid and boron pinacolate) at the 5th position of 1-methyl-5-(trifluoromethyl)-1H-pyrazole was performed based on the direct ortho-metalation (DoM) reaction of 4- bromo-1-methyl-5-(trifluoromethyl)pyrazole followed by catalytic reductive debromination.

Fluorine-containing pyrazole amide derivative, and preparation method and application thereof

The invention discloses a fluorine-containing pyrazole amide derivative, and a preparation method and application thereof. The structural formula of the fluorine-containing pyrazole amide derivative is as described in the invention. In the structural formula, R1 is a trifluoromethyl or difluoromethyl group; R2 is hydrogen, chlorine, fluorine, bromine or iodine; and R3 is polysubstituted benzene orpolysubstituted pyridine. The fluorine-containing pyrazole amide derivative has remarkable antifungal activity and can provide a basis for development of a novel bactericide with the fluorine-containing pyrazole amide compound derivative as an active ingredient.

Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model

Psoriasis is a chronic T-cell-mediated autoimmune disease, and FMS-like tyrosine kinase 3 (FLT3) has been considered as a potential molecular target for the treatment of psoriasis. In this investigation, structural optimization was performed on a lead compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (1), which showed a moderate inhibitory activity againt FLT3. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis led to the discovery of a number of potent FLT3 inhibitors. One of the most active compounds, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (18b), was then chosen for in-depth antipsoriasis studies because this compound displayed the highest potency in a preliminary antipsoriasis test. Compound 18b exhibited significant antipsoriatic effects in the K14-VEGF transgenic mouse model of psoriasis, and no recurrence was found 15 days later after the last administration. Detailed mechanisms of action of compound 18b were also investigated. Collectively, compound 18b could be a potential drug candidate for psoriasis treatment.

PYRIDAZINONE GLUCOKINASE ACTIVATORS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.

KINASE INHIBITORS USEFUL FOR THE TREATMENT OF PROLIFERATIVE DISEASES

The present invention relates to novel kinase inhibitors and modulator compounds useful for the treatment of various diseases. More particularly, the invention is concerned with such compounds, kinase/compound adducts, methods of treating diseases, and methods of synthesis of the compounds. Preferrably, the compounds are useful for the modulation of kinase activity of Raf kinases and disease polymorphs thereof. Compounds of the present invention find utility in the treatment of mammalian cancers and especially human cancers including but not limited to malignant melanoma, colorectal cancer, ovarian cancer, papillary thyroid carcinoma, non small cell lung cancer, and mesothelioma. Compounds of the present invention also find utility in the treatment of rheumatoid arthritis and retinopathies including diabetic retinal neuropathy and macular degeneration.