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

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).

1. stirringstirring
2. waitcontinued at room temperature for 24 h
3. extractionextracted three times with ethyl acetate
4. dry with materialThe combined organic phases were dried over sodium sulfate
5. concentrationconcentrated in vacuo

ORD record

ord-66dad1637cde4b27a1cba9696e4c8464

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06872833B2