Synthesis and characterization of new iminopyridazine butyronitrile hydrobromides

Abstract

In this study, general methods were applied for the preparation of new iminopyridazine butyronitriles. A series of six new 4-(3-aryl-1,6-dihydro-6-iminopyridazin-1-yl)butyronitrile hydro-bromides (2a-2f) (Scheme 1) have been prepared starting from commercially available 3-amino-6-chloropyridazine in two steps with good yields. The synthesized compound’s structures were characterized by IR, 1H NMR and high-resolution mass structures spectral (HRMS) data.
 Journal of Bangladesh Academy of Sciences, Vol. 44, No. 2, 131-138, 2020

Synthesis, characterization and pharmacokinetic studies of 4-(3-aryl-1, 6-dihydro-6-iminopyridazin-1-yl)butanoic acid hydrochlorides

“…The process described in this study involves three steps taking 3-amino-6-chloropyridazine as starting material. Intermediates 1a-1f were synthesized in 22-65% yields using the Suzuki-Miyaura cross-coupling reaction in the presence of Pd (0) catalyst according to previous reports (Maes et al, 2000;Guery et al, 2001;Maes et al, 2002;Rahman et al, 2020) (Scheme 1). We recently reported the synthesis of 1c, 1d, 1e, and 1f (Rahman et al, 2020).…”

“…Intermediates 1a-1f were synthesized in 22-65% yields using the Suzuki-Miyaura cross-coupling reaction in the presence of Pd (0) catalyst according to previous reports (Maes et al, 2000;Guery et al, 2001;Maes et al, 2002;Rahman et al, 2020) (Scheme 1). We recently reported the synthesis of 1c, 1d, 1e, and 1f (Rahman et al, 2020). The maximum yield (65%) was obtained for 3,5-bis (trifluoromethyl) phenyl analog 1f (data are not shown).…”

“…Silica gel column chromatography was applied for purification to yield corresponding 3-amino-6-arylpyridazines 1a-1f. We reported the synthesis of 1c, 1d, 1e, and 1f in a recent study (Rahman et al, 2020), and hence, data are not mentioned here.…”

“…A recent study showed that iminopyridazine butanoic acid derivatives act as competitive antagonists for housefly GABA receptors (Rahman et al, 2021). Recently, we reported the synthesis of several iminopyridazine butyronitrle hydrobromides (Rahman et al, 2020). As gabazine based 3-substituted iminopyridazine of GABA functions as competitive antagonists for insect and mammalian GABA receptors, efforts continue to synthesize iminopyridazine carboxylic acid type compounds.…”