반응 #80122

반응 방정식

4-fluoro-benzoic acid

HATU

N-ethyldiisopropylamine

4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine

hydrochloric acid

→

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

수율 25.2%

용매

THF

dioxane

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued at room temperature for 16 h
3. 3
   추출extracted three times with dichloromethane
4. 4
   건조The combined organic phases were dried over sodium sulfate
5. 5
   농축concentrated in vacuo

실험 절차

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).

출처