Synthesis of 1‐methyl‐4‐(5‐¹⁴C‐3‐methyl‐5‐isoxazolyl) pyridinium chloride

Abstract

l-Methyl-4-(3-methyl-5-isoxazolyl)pyridinium chloride (1) has been found to display interesting hypoglycemic activity in laboratory animals, and is currently undergoing extensive evaluation as a potential antidiabetic drug. To facilitate the study of the bodily distribution and metabolism of 1, a radiolabelled sample was required.

5-Acyl-6-aryl-4-nitro-3(2H)pyridazinones and Related 4-Amino Compounds: Synthesis and Pharmacological Evaluation

“…21 The key intermediates 2 (Table I) were obtained according to literature proceduresl6~18.22~23 (2a-g and 20-p); 2h-1 were synthesized from I d or l b and the appropriate hydrazine; 2m and 2n were synthesized from 2d by Michael-type addition with vinyl reagents of the type CH,=CH-R. The difunctionalized isoxazoles la-c were prepared as previously reported16J8Jg from ethyl chloro(hydroximino)acetatezo and the appropriate 1,3 diketones; the unknown Id was obtained starting from the same hydroximinic chloride and 1-(4-pyridyl)1,3-butandione.…”