Dimethylformamide → N3-(6-nitro-1,3-benzothiazol-2-yl)-2-(4-methoxyanilino)nicotinamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-(4-methoxy phenylamino)nicotinic acid (29, 244 mg 1 mmol) in dry DMF (10 mL) hydroxy benzotriazole HOBt (1.2 mmol) were added at 0° C. After 10 min 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (1.2 mmol) was added and finally 2-amino-6-nitrobenzothiazole (37, 137 mg, 0.7 mmol) were added, then the resulting mixture was stirred at room temperature (27° C.) for 8-10 h and then the reaction mixture was quenched with NaHCO3 and extracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer and dried over anhydrous Na2SO4. The resulting product (5) was purified by column chromatography employing EtOAc/Hexane as an eluent.

Provenance & Evidence