Dimethylformamide → HCID 54613686, compound

Participants

Reaction Conditions

Reaction Steps

Compound 13 (185 mg, 1 mmol) and 3,4,5-methoxy aniline (20, 183 mg, 1 mmol) was taken in ethylene glycol and refluxed at 160° C. for 6 h. Then the reaction mixture was cooled and extracted in ethyl acetate (4×25 mL) from the aqueous layer and concentrated in vacuo. The compound was further purified by column chromatography using 60-120 silica gel (ethyl acetate/hexane, 1:9) to obtain Ethyl 2-(3,4,5-trimethoxy anilino) nicotinate (27) as pure product. Ethyl2-(3,4,5-trimethoxy anilino) nicotinate (27, 332 mg, 1 mmol) were refluxed with 2N NaOH in ethanol for 2 h. The reaction mixture was cooled and left acidified with 2N HCl white solids obtained, filtered and washed with water to give pure compound of 2-(3,4,5-trimethoxyphenylamino) nicotinic acid (34). To a stirred solution of 2-(3,4,5-trimethoxyphenylamino) nicotinic acid (34, 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-fluoro benzothiazole (36, 117 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 (11) was purified by column chromatography employing EtOAc/Hexane as an eluent.

Provenance & Evidence