Thionyl Chloride → N,N-dimethylpyridin-4-amine Hydrochloride

Participants

Reaction Steps

A process for the preparation of the compound of Formula I ##STR10## which comprises Step (a) treating the compound of Formula Va ##STR11## with thionyl chloride in the presence of a 4-N,N'-disubstituted aminopyridine selected from the group consisting of 4-(4-methyl-1-piperidinyl)pyridine; 4-(4-methyl-1-piperidinyl)pyridine hydrochloride; 4-dimethylaminopyridine; and 4-dimethylaminopyridine hydrochloride and a solvent to afford the compound of Formula IVa; ##STR12## Step (b) treating the compound of Formula IVa with sodium isopropoxide in a solvent followed by saponification with a base to afford the compound of Formula III; ##STR13## Step (c) treating the compound of Formula III in a solvent with thionyl chloride and pyridine in a solvent and subsequently adding 5-aminotetrazole and triethylamine in a solvent to afford the compound of Formula II; ##STR14## Step (d) treating the compound of Formula II with sodium hydroxide solution in a solvent to afford the compound of Formula I.

Provenance & Evidence