Ammonia → HCID 18677512, compound

Participants

Reaction Conditions

Reaction Steps

A compound of formula I-3 may be prepared as follows: A solution of 2,6-diamino-isonicotinic acid methyl ester (X) is treated for 1 hour with gaseous ammonia. The mixture is heated for 36 hours at about 60° C. in an autoclave and is then filtered through decalite. The obtained 2,6-diamino-isonicotinamide is suspended in THF and boran-dimethylsulfide-complex (or NaBH4) is added. The mixture is refluxed for 4 days. After cooling to room temperature HCl is added and the mixture is neutralized with NaOH, to give 4-aminomethyl-pyridine-2,6-diamine. A solution of this compound in pyridine is treated with a compound of formula XII together with a catalytic amount of 4-dimethylaminopyridine, and stirred for 2.5 hours at room temperature to obtain a compound of formula III. Furthermore, to the obtained solution of a compound of formula III in dioxane is added O-mesitylenesulfonylhydroxylamine and then an aldehyde of formula V. The mixture is heated to about 100° C. and after 2.5 hours KOH in methanol is added. After stirring the mixture at room temperature a compound of formula I-3 is obtained.

Provenance & Evidence