35808-41-4

Basic information

• Product Name: 1,2,3,4-tetrahydropyrido[3,4-b]pyrazine
• Synonyms: 1,2,3,4-tetrahydropyrido[3,4-b]pyrazine;1,2,3,4-Tetrahydopyridino[3,4-b]pyrazine
• CAS NO: 35808-41-4
• Molecular Formula: C₇H₉N₃
• Molecular Weight: 135.16646
• Mol File: 35808-41-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 318.508°C at 760 mmHg
• Flash Point: 146.429°C
• Appearance: /
• Density: 1.112g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2,3,4-tetrahydropyrido[3,4-b]pyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetrahydropyrido[3,4-b]pyrazine(35808-41-4)
• EPA Substance Registry System: 1,2,3,4-tetrahydropyrido[3,4-b]pyrazine(35808-41-4)

Safety Data

• Hazardous Substances Data: 35808-41-4(Hazardous Substances Data)

Usage

Description

1,2,3,4-Tetrahydropyrido[3,4-b]pyrazine is a heterobicyclic compound with a unique chemical structure that has attracted interest in various fields due to its potential applications and pharmacological properties.

Uses

Used in Pharmaceutical Research:
1,2,3,4-Tetrahydropyrido[3,4-b]pyrazine is used as a compound in the study of aminopyridines, which are relevant to understanding their pharmacokinetics, side effects, and potential antidote effects on botulinum neurotoxin intoxication. This research could lead to the development of new treatments for conditions related to botulinum toxin exposure.
Used in Drug Discovery:
1,2,3,4-Tetrahydropyrido[3,4-b]pyrazine is utilized in a continuous flow strategy for the preparation and elaboration of semi-saturated heterobicyclic fragments. This approach is particularly valuable for fragment-based drug discovery (FBDD) programs, which aim to identify novel drug candidates by studying the interactions between small molecules and biological targets. 1,2,3,4-tetrahydropyrido[3,4-b]pyrazine's unique structure and properties make it a promising candidate for the development of new therapeutic agents.

InChI:InChI=1/C7H9N3/c1-2-8-5-7-6(1)9-3-4-10-7/h1-2,5,9-10H,3-4H2

Upstream product

• 54-96-6 3,4-diaminopyridine 
• 107-21-1 ethylene glycol 
• 254-86-4 pyrido[3,4-b]pyrazine 

Relevant articles and documents

A Continuous Flow Strategy for the Facile Synthesis and Elaboration of Semi-Saturated Heterobicyclic Fragments

An efficient hydrogenation protocol under continuous flow conditions was developed for the synthesis of underrepresented semi-saturated bicyclic fragments containing highly sp3-rich skeletons for fragment-based drug discovery (FBDD) programs. Excellent yields were generally achieved by using Pd/C (10 % w/w) and RaNi at 25–150 °C under 4–100 bar of hydrogen pressure. The generated fragments, with appropriate physicochemical properties, present diverse hydrogen-bonding pharmacophores and useful vectors for their synthetic elaboration in the optimization stage. Successive, simple functionalizations in continuous flow were accomplished to demonstrate the opportunity to develop multi-step continuous flow synthesis of valuable starting points for FBDD campaigns. A conclusive quality control (QC) was essential to discard those structures which do not fit the typical fragment library parameters.

3,4-diaminopyridine derivatives

3,4-Diaminopyridine derivatives corresponding to a specified formula are produced by (a) reacting 3,4-diaminopyridine with a 1,2-dicarbonyl compound to form a diimine; (b) reducing the diimine to a diamine; and (c) replacing at least a hydrogen atom on nitrogen at position 4 of the pyridine ring. These compounds are useful as catalysts.

Modular design of pyridine-based acyl-transfer catalysts

Derivatives of 3,4-diaminopyridine have been synthesized and studied as catalysts for acyl-transfer reactions. The design of these catalysts is guided by the stability of their acetyl intermediates as determined through theoretical calculations at the B3LYP/6-311 + G(d,p)//B3LYP/6-31G(d) level of theory. The most promising catalysts have been synthesized through a three- to five-step synthesis starting from 3,4-diaminopyridine. The catalytic activity has been determined for the acylation of 1-ethynylcyclohexanol with acetic anhydride at 23°C and with isobutyric anhydride at 40°C. For both reactions, the catalytic activity depends dramatically on the substitution pattern of the diaminopyridines. Best results are obtained with catalysts containing alkyl substituents at both amine nitrogens. Georg Thieme Verlag Stuttgart.