Application examples of 1-(4-chloropyridine)-2-piperazine_Industrial additives

Background and overview of application examples of 1-(4-chloropyridine)-2-piperazine

1-(4-chloropyridine)-2-piperazine can be used as a pharmaceutical synthesis intermediate and can be used to prepare sigma-2 receptor adhesives and mGlu receptor modulators.

Application examples of 1-(4-chloropyridine)-2-piperazine

Application example report 1 of 1-(4-chloropyridine)-2-piperazine,

Preparation of 3-(2-(4-(4-chloropyridin-2-yl)piperazin-1-yl)ethyl)-2-oxo from 1-(4-chloropyridin)-2-piperazine Heterospir[4.4]nonanon-1-one, this compound can be used as a sigma-2 receptor binder for the treatment of diseases related to dysregulation of sigma-2 receptor activity. The preparation method is as follows:

To the vial, add 2-(1-oxo-2-oxaspiro[4.4]nonyl-3-yl)ethylethyl 4-methylbenzenesulfonate (50 mg, 0.15 mmol, 1.0 equiv) and dissolve it in 5 mL of tetrahydrofuran. Then 1-(4-chloropyridine)-2-piperazine (58 mg, 0.30 mmol, 2.0 equiv) was added. The reaction was stirred at 60°C for 3 days. The solution was allowed to cool to room temperature and then diluted with deionized water (5 mL) and ethyl acetate (5 mL). The layers were separated, and the aqueous layer was washed with 2 × methoxyphenylboronic acid; 5 mL of ethyl acetate. The organic layers were combined and dried over Na₂SO₄ and concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography (silica gel; methanol/dichloromethane, 0-10%). ¾NMR(MHz,chloroform-d)δ7.96(d,J=6.0Hz,1H),6.58(d,J=2.3Hz,1H),6.50(dd,J=6.0,2.3Hz,1H),4.42( m,1H),3.29(br,4H),2.53(br,6H),2.18(m,2H),1.85-1.55(m,10H). Boric acid LC/MSM+l=364.20.

Application example report 2 of 1-(4-chloropyridine)-2-piperazine,

1-(4-chloropyridine)-2-piperazine can also be used to prepare mGlu receptor modulators with the following structure. Glutamic acid is the major excitatory amino acid in the mammalian central nervous system. Glutamate-mediated neurotransmission has been shown to be critical in many physiological processes, such as synaptic plasticity, involved in long-term enhancement of learning and memory, and sensory perception. Furthermore, imbalances in glutamate neurotransmission have been shown to play a critical role in the pathophysiology of various neurological and psychiatric disorders.

References

[1]WO2016183150-NOVEL SIGMA-2 RECEPTOR BINDERS AND THEIR METHOD OF USE

[2]US20130184248-SUBSTITUTED TRIAZOLESUSEFULA SMGLU5 RECEPTOR MODULATORS