Diisopropylethylamine → N-[4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-yl]-2-methyl-isonicotinamide

Participants

Reaction Steps

To a stirred solution of 111 mg (0.40 mmol) 4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-ylamine and 0.26 ml (1.50 mmol) N-ethyldiisopropylamine in 20 ml THF at room temperature was added dropwise a solution of 127 mg (0.66 mmol) 2-methyl-isonicotinoyl chloride hydrochloride in 20 ml dichloromethane and stirring continued at room temperature for 24 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (3/97 methanol/ethyl acetate) followed by trituration in ether afforded 142 mg (90%) N-[4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-yl]-2-methyl-isonicotinamide as a yellow crystalline solid. ES-MS m/e (%): 419 (M+Na+, 17), 397 (M+H+, 100).

Provenance & Evidence