37801-57-3

Basic information

• Product Name: ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE
• Synonyms: ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE
• CAS NO: 37801-57-3
• Molecular Formula: C₁₀H₁₀ClN₃O₂
• Molecular Weight: 239.66
• Mol File: 37801-57-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 336.3°C at 760 mmHg
• Flash Point: 157.2°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.633
• PKA: 1.43±0.30(Predicted)
• CAS DataBase Reference: ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE(37801-57-3)
• EPA Substance Registry System: ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE(37801-57-3)

Safety Data

• Hazardous Substances Data: 37801-57-3(Hazardous Substances Data)

Usage

General Description

ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE is a chemical compound with the molecular formula C11H9ClN4O2. It is a pyrazolo[3,4-b]pyridine derivative with an ethyl ester functional group. ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE is commonly used in the field of medicinal chemistry and pharmaceutical research as a building block for the synthesis of various biologically active molecules. Its unique structure and properties make it a valuable intermediate for the development of new drugs and potentially useful in the treatment of various diseases and disorders. Additionally, it may also have potential applications in agrochemicals and materials science.

InChI:InChI=1/C10H10ClN3O2/c1-3-16-10(15)7-4-12-9-6(8(7)11)5-13-14(9)2/h4-5H,3H2,1-2H3

Upstream product

• 37799-77-2 diethyl 2-[(1-methyl-1H-pyrazol-5-ylamino)methylene]malonate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 1192-21-8 5-Amino-1-methylpyrazole 

Downstream Products

• 675111-88-3 4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 
• 675111-93-0 N-benzyl-4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide 

Relevant articles and documents

Identification of pyrazolopyrimidine arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists

A novel 4-aminoindazole sulfonamide hit (13) was identified as a human CCR4 antagonists from testing a focussed library of compounds in the primary GTPγS assay. Replacing the indazole core with a pyrazolopyrimidine, and introduction of a methoxy group adjacent to the sulfonamide substituent, resulted in the identification of pyrazolopyrimidine 37a, which exhibited good binding affinity in the GTPγS assay (pIC50 = 7.2), low lipophilicity (c log P = 2.2, chromlog D7.4 = 2.4), high LE (0.41), high solubility (CLND solubility ≥581 μM), and an excellent PK profile in both the rat (F = 62%) and the dog (F = 100%). Further SAR investigation of the pyrazolopyrimidine suggested that substitution at N1 is tolerated, providing a suitable vector to modulate the properties, and increase the potency in a lead optimisation campaign.

PYRAZOLO[3,4-B]PYRIDINE COMPOUNDS, AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS

The invention relates to a compound of formula (I) or a salt thereof: wherein:R1 is C1-4alkyl, C1-3fluoroalkyl, -CH2CH2OH or -CH2CH2CO2C1-2alkyl;R2 is a hydrogen atom (H), methyl or C1fluoroalkyl;R3 is optionally substituted C3-8cycloalkyl or optionally substituted mono-unsaturated-C5-7cycloalkenyl or an optionally substituted heterocyclic group of sub-formula (aa), (bb) or (cc); in which n1 and n2 independently are 1 or 2; and in which Y is O, S, SO2, or NR10; or R3 is a bicyclic group (dd) or (ee): ; and wherein X is NR4R5 or OR5a. The compounds are phosphodiesterase (PDE) inhibitors, in particular PDE4 inhibitors. Also provided is the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and/or prophylaxis of an inflammatory and/or allergic disease in a mammal such as a human, for example chronic obstructive pulmonary disease (COPD), asthma, or allergic rhinitis.