27258-33-9

Usage

Uses

Used in Organic Synthesis:
1-Methyl-1H-pyrazole-5-carbaldehyde is used as a building block in organic synthesis for the preparation of various pharmaceutical and agrochemical compounds. Its aldehyde group makes it a versatile intermediate for the synthesis of heterocyclic compounds, which are widely used in medicinal chemistry.
Used in Medicinal Chemistry:
1-Methyl-1H-pyrazole-5-carbaldehyde is used as a key intermediate in the development of heterocyclic compounds with potential applications in medicinal chemistry. These compounds can be further modified and optimized for specific therapeutic targets, contributing to the discovery of new drugs.
Used in Materials Science:
1-Methyl-1H-pyrazole-5-carbaldehyde has potential applications in the field of materials science, particularly in the development of new functionalized materials and polymers. Its unique structure and reactivity can be utilized to create novel materials with desired properties for various applications.

InChI:InChI=1/C5H6N2O/c1-7-5(4-8)2-3-6-7/h2-4H,1H3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 67751-23-9 4-(dimethylamino)-1,1-dimethoxy-but-3-en-2-one 
• 60-34-4 methylhydrazine 
• 1269291-90-8 5-(dimethoxymethyl)-1-methyl-1H-pyrazole 
• 930-36-9 1-methyl-1H-pyrazole 

Downstream Products

• 313753-40-1 methyl 7-{4-[2-(butoxy)ethoxy]phenyl}-1-[(1-methyl-1H-pyrazol-5-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate 
• 148408-72-4 (R)-(+)-1-Methyl-α-phenyl-1H-pyrazole-5-methanol 
• 1159185-85-9 4-(3-(5-chloro-6-(1-methyl-1H-pyrazole-5-carbonyl)pyridin-3-ylthio)phenyl)-tetrahydro-2H-pyran-4-carboxamide 
• 874278-23-6 C₂₆H₃₂N₆ 
• 911491-59-3 C₂₂H₂₅FN₆O₃ 
• 16034-46-1 1-methyl-1H-pyrazole-5-carboxylic acid 
• 473528-88-0 4-bromo-1-methyl-1H-pyrazole-5-carboxaldehyde 
• 1276056-83-7 (4-bromo-1-methyl-1H-pyrazol-5-yl)methanol 
• 796845-51-7 tert-butyl 2-(1-methylpyrazol-5-yl)ethylcarbamate 
• 1006493-80-6 N-[(1-methyl-1H-pyrazol-5-yl)methyl]-4-(trifluoromethyl)aniline 
• 313752-00-0 7-{4-[2-(butoxy)ethoxy]phenyl}-1-[(1-methyl-1H-pyrazol-5-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid 
• 351529-78-7 (RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(5-tert-butyldimethylsilyloxymethyl-1-methylpyrazol-4-yl)methanol 
• 164162-17-8 (2R,4R)-1-allyloxycarbonyl-4-benzoylthio-2-[(5-hydroxymethyl-1-methylpyrazol-4-yl)methyl]pyrrolidine 

Relevant academic research and scientific papers

MATRIX METALLOPROTEINASE (MMP) INHIBITORS AND METHODS OF USE THEREOF

Hydantoin based compounds useful as inhibitors of matrix metalloproteinases (MMPs), particularly macrophage elastase (MMP-12) are described. Also described are related compositions and methods of using the compounds to inhibit MMP-12 and treat diseases mediated by MMP-12, such as asthma, chronic obstructive pulmonary disease (COPD), emphysema, acute lung injury, idiopathic pulmonary fibrosis (IPF), sarcoidosis, systemic sclerosis, liver fibrosis, nonalcoholic steatohepatitis (NASH), arthritis, cancer, heart disease, inflammatory bowel disease (IBD), acute kidney injury (AKI), chronic kidney disease (CKD), Alport syndrome, and nephritis.

MATRIX METALLOPROTEINASE (MMP) INHIBITORS AND METHODS OF USE THEREOF

Hydantoin based compounds useful as inhibitors of matrix metalloproteinases (MMPs), particularly macrophage elastase (MMP-12) are described. Also described are related compositions and methods of using the compounds to inhibit MMP-12 and treat diseases mediated by MMP-12, such as asthma, chronic obstructive pulmonary disease (COPD), emphysema, acute lung injury, idiopathic pulmonary fibrosis (IPF), sarcoidosis, systemic sclerosis, liver fibrosis, nonalcoholic steatohepatitis (NASH), arthritis, cancer, heart disease, inflammatory bowel disease (IBD), acute kidney injury (AKI), chronic kidney disease (CKD), Alport syndrome, and nephritis.

Preparation method of 2-(4-bromo-1-methyl-1H-pyrazol-5-yl)ethanamine

The invention relates to a preparation method of 2-(4-bromo-1-methyl-1H-pyrazol-5-yl)ethanamine. The method comprises the following steps: reacting 1-methylpyrazole used as a raw material to obtain 1-methyl-1H-pyrazole-5-carbaldehyde; adding piperidine and pyridine to obtain a solid 3-(1-methyl-1H-pyrazole-5-yl) acrylic acid; further, adding palladium on carbon into a methanol solution, and introducing hydrogen to obtain 3-(1-methyl-1H-pyrazol-5-yl) propionic acid; furthermore, reacting under roles of bromine and saturated sodium sulphite solution, and performing spinning drying to obtain a solid 3-(4-bromo-1-methyl-1H-pyrazol-5-yl) propionic acid; adding thionyl chloride, tetrahydrofuran, and stronger ammonia water, reacting, dissolving out methyl alcohol, purifying silica gel, eluting ethyl acetate in sequence to obtain 3-(4-bromo-1-methyl-1H-pyrazol-5-yl) propanamide; finally adding NaOH and bromine, and performing ice-bath to obtain 2-(4-bromo-1-methyl-1H-pyrazol-5-yl)ethanamine. The method has the advantages of being clear in steps, little in waste, high in yield, easy to operate and capable of saving raw materials.

PYRIMIDINE PDE10 INHIBITORS

The present invention is directed to pyrimidine compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

Spin transition in the molecular heterospin complex of Cu(hfac)2 with 4,4,5,5-tetramethyl-2-(1-methylpyrazol-5-yl)-4,5-dihydroimidazole-1-oxyl 3-oxide

The synthesis, structure, and magnetic properties of the products of the reaction for Cu(hfac)2 (hfac is hexafluoroacetylacetonate) with spin-labeled nitronyl nitroxides 4,4,5,5-tetramethyl-2-(1-R-1H-pyrazol-5-yl)-3- imidazoline-1-oxyl 3-oxides L5/R (R = Me, Et, Pr, Bu), viz., binuclear complex [Cu(hfac)2L5/Me]2 and chain polymer complexes [Cu(hfac)2L5/R]n, are described. The polymer heterospin chains are built according to head-to-head (R = Me, Et, Pr, Bu) and head-to-tail (R = Pr, Bu) motifs. Compound [Cu(hfac)2L5/Me]2 is characterized by the ability to reveal the reversible effect of thermally induced spin transition at a temperature about 75 K (without hysteresis). In the set of heterospin CuII compounds with spin-labeled pyrazoles, this is the earlier unknown example of a molecular complex exhibiting a similar magnetic anomaly.

Combination of two pharmacophoric systems: Synthesis and pharmacological evaluation of spirocyclic pyranopyrazoles with high σ1 receptor affinity

The novel class of spirocyclic σ1 ligands 3 (6′,7′-dihydro-1′H-spiro[piperidine-4,4′-pyrano[4,3-c] pyrazoles]) was designed by the combination of the potent σ1 ligands 1 and 2 in one molecule. Thorough structure affinity relationship

Method for the Production of N-Substituted (3-Dihalomethyl-1-Methyl-Pyrazole-4-yl) Carboxamides

The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R1 is optionally substituted phenyl or C3-C7-cycloalkyl, R1a is hydrogen or fluorine, or R1a together with R1 is optionally substituted C3-C5-alkanediyl or C5-C7-cycloalkanediyl, R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C4-alkoxy-C1-C2-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R1, R1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

Spiro-pyrano-pyrazole derivatives

The present invention relates to compounds of formula (I) having pharmacological activity towards the sigma (σ) receptor, and more particularly to some spiro-pyrano-pyrazole derivatives, to processes of preparation of such compounds, to pharmaceutical com

PYRAZOLE DERIVATIVES AS P2X7 MODULATORS

The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein R1 represents C1-6 alkyl or C3-6 cycloalkyl, either of which is optionally substituted with 1, 2 or 3 ha

PROCESS FOR OBTAINING ENANTIOMERS OF THIENYLAZOLYLALCOXYETHANAMINES

A process is described for the preparation of a precursor alcohol of (±)-2-[thienyl(1-methyl-1H-pyrazol-5-yl)methoxy]-N,N-dimethyletanamine and in general for thienylazolylalcoxyethanamines and their enantiomers. The process involves asymmetric addition of a metalated thienyl reagent to a pyrazolcarbaldehyde in the presence of a chiral ligand to yield chiral alcohols. The chiral alcohols are further O-alkylated to yield the corresponding pharmaceutically active thienylazolylalcoxyethanamines.