Diisopropylethylamine → (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Participants

Reaction Steps

To a stirred solution of 296 mg (1.46 mmol) 2-bromo-isonicotinic acid in 10 ml THF were added 642 mg (1.69 mmol) HATU and 0.29 ml (1.69 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 1 h. 300 mg (1.13 mmol) (±)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine was then added and stirring continued at room temperature for 24 h. The reaction mixture was then poured into saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 370 mg (73%) (±)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide as a light yellow solid. ES-MS m/e (%):452 (M{81Br}+H+, 100), 450 (M{79Br}+H+, 95).

Provenance & Evidence