Pyridine → 7-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide

温度

155 °C

A mixture of 7-bromoisoquinoline (6.5 g, 31.24 mmol) in HSO3Cl (60 mL) is heated to 155° C. with stirring under N2 overnight, and then cooled to room temperature and slowly poured into ice water. After neutralizing with NaHCO3 at 0° C., sulfonyl chloride is extracted with methylene chloride. The organic layer is dried over Na2SO4 and concentrated to 100 mL and dropped to a solution of N-t-butoxycarbonylethylene diamine (5.01 g, 31.24 mmol) in pyridine (2.54 mL, 31.24 mmol) and CH2Cl2 (120 mL). After stirring overnight, the mixture is concentrated, and the residue is dissolved in EtOAc, which is washed with citric acid solution (50%) and brine. The crude material is purified by chromatography over silica gel (gradient 20% hexane in EtOAc) to give 6.50 g (50% yield) of desired product

1. temperaturecooled to room temperature
2. extractionsulfonyl chloride is extracted with methylene chloride
3. dry with materialThe organic layer is dried over Na2SO4
4. concentrationconcentrated to 100 mL
5. stirringAfter stirring overnight
6. concentrationthe mixture is concentrated
7. dissolutionthe residue is dissolved in EtOAc
8. washwhich is washed with citric acid solution (50%) and brine
9. customThe crude material is purified by chromatography over silica gel (gradient 20% hexane in EtOAc)

ORDレコード

ord-fa0fb79887d646c5b27ca47b1d14f14a

出典データセット

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07449477B2