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

To a stirred solution of 503 mg (2.93 mmol) 2-chloromethyl-isonicotinic acid in 50 ml THF were added 1.28 g (3.38 mmol) HATU and 0.96 ml (5.63 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 2 h. 600 mg (2.25 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. Flash chromatography (acetone) followed by trituration in ether afforded 450 mg (48%) (+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide as a light yelllow solid. [α]D20=+12.1° (c=0.41, CHCl3), ES-MS m/e (%):422 (M{37Cl}+H+, 35), 420 (M{35Cl}+H+, 100).

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レコード

ord-d48f015c53224fdca28ae3127ed71510

出典データセット

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06872833B2