4077-76-3

Basic information

• Product Name: Dimethyl 1H-pyrazole-3,5-dicarboxylate
• Synonyms: 1H-Pyrazole-3,5-dicarboxylic acid 3,5-dimethyl ester;1H-Pyrazole-3,5-dicarboxylic acid dimethyl ester;3,5-Bis(methoxycarbonyl)pyrazole;3,5-Dicarbomethoxypyrazole;Dimethyl 3,5-pyrazoledicarboxylate;Pyrazole-3,5-dicarboxylic acid dimethyl ester;3,5-Bis(methoxycarbonyl)-1H-pyrazole;Dimethyl 1H-pyrazol-3,5-dicarboxylate
• CAS NO: 4077-76-3
• Molecular Formula: C₇H₈N₂O₄
• Molecular Weight: 184
• Mol File: 4077-76-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 151-152℃
• Boiling Point: 344℃
• Flash Point: 162℃
• Appearance: /
• Density: 1.346
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.08±0.10(Predicted)
• CAS DataBase Reference: Dimethyl 1H-pyrazole-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 1H-pyrazole-3,5-dicarboxylate(4077-76-3)
• EPA Substance Registry System: Dimethyl 1H-pyrazole-3,5-dicarboxylate(4077-76-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4077-76-3(Hazardous Substances Data)

Usage

Description

Dimethyl 1H-pyrazole-3,5-dicarboxylate is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is characterized by its unique structure, which features a pyrazole ring with two carboxyl groups and two methyl ester groups attached to the adjacent positions on the ring. Dimethyl 1H-pyrazole-3,5-dicarboxylate is known for its versatile reactivity and ability to form a wide range of derivatives, making it a valuable building block in the development of new drugs and other applications.

Uses

Used in Pharmaceutical Industry:
Dimethyl 1H-pyrazole-3,5-dicarboxylate is used as a key intermediate in the synthesis of substituted dihydropyrazolopyrazinecarboxamide derivatives. These derivatives have been identified as EP3 receptor antagonists, which are useful for treating various diseases. By modulating the activity of the EP3 receptor, these antagonists can help regulate inflammatory processes and provide therapeutic benefits in the treatment of conditions such as chronic pain, inflammatory disorders, and other related diseases.

Upstream product

• 67-56-1 methanol 
• 3112-31-0 3,5-pyrazoledicarboxylic acid 
• 152327-57-6 dimethyl (E)-3-diazo-1-propene-1,3-carboxylate 
• 5164-76-1 dimethyl glutaconate 
• 123-54-6 acetylacetone 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 19255-80-2 5-methoxycarbonyl-pyrazoline-3-carboxylic acid methyl ester 
• 1729-67-5 Methyl 2,3-dibromopropionate 
• 6832-16-2 methyl diazoacetate 
• 4519-46-4 methyl 2-bromoacrylate 
• 80-63-7 methyl 2-chloroacrylate 

Downstream Products

• 232281-30-0 methyl 3-cyano-1-methyl-1H-pyrazole-5-carboxylate 
• 117860-56-7 5-(methoxycarbonyl)-1-methyl-1H-pyrazole-3-carboxylic acid 
• 33146-99-5 methyl ester of 1-methylpyrazole-3,5-dicarboxylic acid 

Relevant articles and documents

Structure of 2,4,4,5,5-pentamethyl-2-imidazoline-1-oxyl-3-oxide

The crystal and molecular structures of the stable nitroxide radical 2,4,4,5,5-pentamethyl-2-imidazoline-1-oxyl-3-oxide was determined. The N-O bond lengths are 1.279(2) and 1.280(2) A, respectively. The O --N+=C-N-?O fragment is nearly planar with carbon atoms of the ethyl fragment that deviated from the O-N+=C-N-?O plane by -0.204(5) and +0.176(5) A. The minimum intermolecular distance between the oxygen atoms of NO groups is 4.094 A.

FUSED RING PYRIMIDONE DERIVATIVES FOR USE IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES

Provided are compounds according to any of Formula (I-1) to (I-7), pharmaceutical compositions comprising at least one of said compounds, their use as a medicament, and their use in treating chronic hepatitis B virus (HBV) infection. Methods for preparing compounds according to any of Formula (I-1) to (I-7) are also provided.

Optimization of Novel 1-Methyl-1 H-Pyrazole-5-carboxamides Leads to High Potency Larval Development Inhibitors of the Barber's Pole Worm

A phenotypic screen of a diverse library of small molecules for inhibition of the development of larvae of the parasitic nematode Haemonchus contortus led to the identification of a 1-methyl-1H-pyrazole-5-carboxamide derivative with an IC50 of 0.29 μM. Medicinal chemistry optimization targeted modifications on the left-hand side (LHS), middle section, and right-hand side (RHS) of the scaffold in order to elucidate the structure-activity relationship (SAR). Strong SAR allowed for the iterative and directed assembly of a focus set of 64 analogues, from which compound 60 was identified as the most potent compound, inhibiting the development of the fourth larval (L4) stage with an IC50 of 0.01 μM. In contrast, only 18% inhibition of the mammary epithelial cell line MCF10A viability was observed, even at concentrations as high as 50 μM.