Hydrochloric Acid → 4-fluoro-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide

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Reaction Steps

To a stirred solution of 79 mg (0.56 mmol) 4-fluoro-benzoic acid in 10 ml THF were added 235 mg (0.62 mmol) HATU and 0.11 ml (0.62 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 1 h. A solution of 150 mg (0.56 mmol) 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine in 5 ml dioxane and 1 ml DMF was then added and stirring continued at room temperature for 16 h. The reaction mixture was then poured into 100 ml 1 M hydrochloric acid and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/4-1/1 ethyl acetate/hexane) followed by trituration in hexane afforded 55 mg (25%) 4-fluoro-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide as an off-white crystalline solid. ES-MS m/e (%): 390 (M+H+, 100).

Provenance & Evidence