89582-17-2

Usage

Uses

Used in Pharmaceutical Industry:
6-Methyl-[1,4]diazepane is used as a reactant in the preparation of imidazopyridines, which are a class of compounds with potential therapeutic applications. Specifically, these imidazopyridines are being developed for the treatment of pain and pain-related conditions. The incorporation of 6-Methyl-[1,4]diazepane into the molecular structure of imidazopyridines is crucial for their pharmacological properties and effectiveness in managing pain.

InChI:InChI=1/C6H14N2/c1-6-4-7-2-3-8-5-6/h6-8H,2-5H2,1H3

Upstream product

• 78-85-3 2-methylpropenal 
• 107-15-3 ethylenediamine 

Downstream Products

• 1439358-16-3 C₁₉H₂₅N₅O₃S 

Relevant academic research and scientific papers

HOMOPIPERAZINYL AND HOMOPIPERIDINYL QUINAZOLIN-4(3H)-ONE DERIVATIVES HAVING MULTIMODAL ACTIVITY AGAINST PAIN

The present invention relates to homopiperazinyl and homopiperidinyl quinazolin- 4(3H)-one derivatives having dual pharmacological activity towards both the α2δ subunit of the voltage-gated calcium channel and the sigma-1 (σ1) receptor, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy, in particular for the treatment of pain.

NMR study of stereoelectronic anomeric and homoanomeric effects on the axial and equatorial CH bonds in 1,3-diazacyclohexanes and 1,5-diazabicyclo[3.2.1]octanes

The 1H and 13C NMR spectra of a series of 1,3-di-tert-butyl-1,3-diazacyclohexanes 6, and of 1,5-diazabicyclo[3.2.1]octanes 7, have been investigated in an attempt to find evidence regarding a stereoelectronic interaction of the non-bonding electron pairs on nitrogen or of the C-N bonding electron pairs in the ring, with the axial and equatorial CH bonds of the α- or β-methylene groups. In 6, the orbital carrying the non-bonding electron pair lies antiperiplanar to the axial α-CH bond; a significant nN→σ*CH 3-orbital interaction (the anomeric effect) is sterically possible, and this shows up in the values of δH and of 1JCH. In 7, the doubly-occupied orbital is orientated gauche to both the axial and equatorial α-CH bonds, and no anomeric effect is apparent. In 7 however, in contrast to 6, the stereochemistry is appropriate for a W-plan nN→σ*CH 4-orbital interaction with the equatorial β-CH bond, and comparison of the NMR data of 6 and 7 suggests that such a homoanomeric effect may operate, though it is much weaker than in the analogous 1,3-dioxanes. No evidence could be found for a σCN→σ*CH 3-orbital interaction.