3-Chloro-2,4-pentanedione → 5-Acetyl-2-amino-4-methylthiazole

Participants

Reaction Steps

An efficient route for the synthesis bithiazole analogs was developed as follows. Efforts began with a synthesis of N-(2-(5-chloro-2-methoxyphenylamino)-4′-methyl-4,5′-bithiazol-2′-yl)benzamide—the putative structure of “Corr-4” corrector 4. This work commenced by treating 3-chloropentane-2,4-dione with thiourea under reflux in absolute ethanol. 5-Acetyl-2-amino-4-methylthiazole (5) was obtained in 90% yield. Surprisingly, attempts to aminoacylate the 2-amino moiety in 5 with benzoyl chloride under various base, solvent and temperature conditions failed to deliver the desired intermediate N-(5-acetyl-4-methyl-thiazol-2-yl)-benzamide (6).

Provenance & Evidence