1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[6-(2-Ethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester

To a stirred solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (V), (1.27 g, 5.54 mmol) in dry dichloromethane, HOBt (1.27 g, 9.30 mmol) and EDCI (1.78 g, 9.30 mmol) were added at 0° C. and the reaction mixture was stirred for 5-10 minutes. Then 6-(2-ethoxy-phenyl)-pyrimidin-4-ylamine (III) (1.00 g, 4.65 mmol) was added and the reaction mixture was heated to reflux under an atmosphere of nitrogen for 48 hours. The reaction mixture was diluted with dichloromethane and washed with 1N HCl, aqueous sodium bicarbonate, water and brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by column chromatography to obtain 4-[6-(2-ethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (IV) (0.79 g, 40%).

1. temperaturethe reaction mixture was heated
2. temperatureto reflux under an atmosphere of nitrogen for 48 hours
3. washwashed with 1N HCl, aqueous sodium bicarbonate, water and brine
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was removed under reduced pressure
6. customthe crude product was purified by column chromatography

ORDレコード

ord-61ee97484cd54488a6f3bbe7ed8aa71d

出典データセット

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08716296B2