21056-77-9

Basic information

• Product Name: ethyl 1H-pyrazole-5(3)-carboxylate
• Synonyms: ethyl 1H-pyrazole-5(3)-carboxylate;EOS-62297
• CAS NO: 21056-77-9
• Molecular Formula: C₆H₈N₂O₂
• Mol File: 21056-77-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 1H-pyrazole-5(3)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1H-pyrazole-5(3)-carboxylate(21056-77-9)
• EPA Substance Registry System: ethyl 1H-pyrazole-5(3)-carboxylate(21056-77-9)

Safety Data

• Hazardous Substances Data: 21056-77-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Ethyl 1H-pyrazole-5(3)-carboxylate is used as a building block for the synthesis of various organic compounds, leveraging its reactivity and unique chemical structure to facilitate the creation of a wide range of products.
Used in Medicinal Chemistry:
In the pharmaceutical industry, ethyl 1H-pyrazole-5(3)-carboxylate is employed as a key intermediate in the development of new drugs, contributing to the design and synthesis of therapeutic agents with potential applications in treating various diseases and conditions.
Used in Agrochemical Development:
Ethyl 1H-pyrazole-5(3)-carboxylate is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, due to its ability to enhance the effectiveness and selectivity of these compounds in agricultural applications.
Used in Dye and Pigment Synthesis:
In the dye and pigment industry, ethyl 1H-pyrazole-5(3)-carboxylate is used as a starting material for the production of pyrazole-based dyes and pigments, offering a range of color options and properties for various applications, including textiles, plastics, and inks.

Upstream product

• 64-17-5 ethanol 
• 1621-91-6 1H-pyrazole-3-carboxylic acid 
• 1621-91-6 1-2H-pyrazole-3-carboxylic acid 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 181427-25-8 ethyl (E)-4-(dimethylamino)-2-oxo-but-3-enoate 
• 59938-07-7 (3E)-1,1,1-trichloro-4-ethoxybut-3-en-2-one 

Downstream Products

• 1313409-96-9 ethyl 1-(4-methoxybenzyl)-1H-pyrazole-5-carboxylate 
• 951626-38-3 6,7-dihydro-pyrazolo[1,5-a] pyrazin-4(5H)-one 
• 1621-91-6 1-2H-pyrazole-3-carboxylic acid 
• 115315-94-1 ethyl 1-phenyl-1H-pyrazole-5-carboxylate 
• 174907-58-5 ethyl 1-benzyl-1H-pyrazole-3-carboxylate 

Relevant articles and documents

JNK inhibitor as well as pharmaceutical composition and application thereof

The invention provides a compound represented by a formula (I), racemates, stereoisomers, tautomers, isotope markers, solvates, polymorphic substances, nitrogen oxides, or pharmaceutically acceptablesalts thereof, and application as a JNK inhibitor. The invention also provides a preparation method of the compound shown in the formula (I), a pharmaceutical composition containing the compound shownin the formula (I), and application of the compound shown in the formula (I) to preparation of a medicine, and the medicine is used for treating diseases which can be treated by inhibiting the activity of JNK.

Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: N-versus C-Attack Paths

Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.

Discovery of novel fragments inhibiting O-acetylserine sulphhydrylase by combining scaffold hopping and ligand–based drug design

Several bacteria rely on the reductive sulphur assimilation pathway, absent in mammals, to synthesise cysteine. Reduction of virulence and decrease in antibiotic resistance have already been associated with mutations on the genes that codify cysteine biosynthetic enzymes. Therefore, inhibition of cysteine biosynthesis has emerged as a promising strategy to find new potential agents for the treatment of bacterial infection. Following our previous efforts to explore OASS inhibition and to expand and diversify our library, a scaffold hopping approach was carried out, with the aim of identifying a novel fragment for further development. This novel chemical tool, endowed with favourable pharmacological characteristics, was successfully developed, and a preliminary Structure–Activity Relationship investigation was carried out.

6,7-DIHYDROPYRAZOLO[1,5-A]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS

The present invention relates to novel 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 ("mGluR2"). The invention is also directed to pharmaceutical compositi

6,7-DIHYDROPYRAZOLO[1,5-A]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS

The present invention relates to novel 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 ("mGluR2"). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention or treatment of disorders in which the mGluR2 subtype of metabotropic receptors is involved.

6,7-DIHYDROPYRAZOLO[1,5-α]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS

The present invention relates to novel 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 ("mGluR2"). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention or treatment of disorders in which the mGluR2 subtype of metabotropic receptors is involved.

RADIOLABELLED MGLUR2 PET LIGANDS

The present invention relates to novel, selective, radiolabelled mGluR2 ligands which are useful for imaging and quantifying the metabotropic glutamate receptor mGluR2 in tissues, using positron-emission tomography (PET). The invention is also directed to compositions comprising such compounds, to processes for preparing such compounds and compositions, to the use of such compounds and compositions for imaging a tissue, cells or a mammal, in vitro or in vivo and to precursors of said compounds.

6,7-DIHYDROPYRAZOLO[1,5-a]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS

The present invention relates to novel 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives of Formula (I) as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 ("mGluR2"). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention or treatment of disorders in which the mGluR2 subtype of metabotropic receptors is involved, especially CNS disorders.

SUBSTITUTED N-(1H-INDAZOL-4-YL)IMIDAZO[1, 2-A]PYRIDINE-3- CARBOXAMIDE COMPOUNDS AS CFMS INHIBITORS

Compounds of Formula (I): and pharmaceutically acceptable salts thereof in which R1, R2, R3, R4 and R5 have the meanings given in the specification, are inhibitors of cFMS and are useful in the treatment of bone-related diseases, cancer, autoimmune disorders, inflammatory diseases, cardiovascular diseases and pain.

Regioselective synthesis of ethyl pyrazolecarboxylates from ethyl 3-[(dimethylamino)methylidene]pyruvate and diethyl 3-[(dimethylamino)methylidene]-2-oxosuccinate. Isolation of ethyl 4,5-dihydro-1-heteroaryl-5-hydroxy-1H-pyrazole-5-carboxylates as stable intermediates in the pyrazole ring formation

Reactions of ethyl 3-[(E)-(dimethylamino)methylidene]pyruvate (3) and 3-[(dimethylamino)methylidene]-2-oxosuccinate (4) with hydrazine monohydrochloride (5a) and (hetero)arylhydrazines (5b-i) afforded, regioselectively, 1-substituted ethyl 1H-pyrazole-5-carboxylates 9a-f and diethyl 1H-pyrazole-3,4-dicarboxylates, 11a-i, respectively. Upon treatment of 3 with pyridazinylhydrazines 5d-f, the stable intermediates, 1-substituted ethyl 4,5-dihydro-5-hydroxy-1H-pyrazole-5-carboxylates 8d-f, were isolated. Treatment of compounds 8d-f in acetic acid under reflux furnished the pyrazoles 9d-f. On the other hand, reaction of 3 with N,N′-dimethylhydrazine (5I) gave ethyl 1-methyl-1H-pyrazole-3-carboxylate (14). The structures of compounds 3, 4, 14 were determined by nmr (noesy and hmbc techniques), while the structures of compounds 8f, 9f, and 11e,f were determined by X-ray diffraction.