Diethylene Glycol → 3-Amino-5-chloro-6-[2-(2-hydroxy-ethoxy)-ethoxy]-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

温度

75 °C

To a solution of diethylene glycol (1.118 g, 10.54 mmol) in THF (3 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes) (3.50 ml, 3.50 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.345 g, 1.00 mmol). The reaction mixture is heated at 75° C. for 1 hour, cooled to room temperature, and then quenched by the addition of water (15 ml). Ice is added to the reaction mixture and, while stirring, a yellow precipitate is formed. This solid is collected by filtration and placed in the vacuum oven to dry (60° C. for 16 hours). This affords the title compound as a yellow solid (0.150 g, 39%). Mass (m/z): 386.2 (M++1), 384.1 (M+−1).

1. temperaturecooled to room temperature
2. customquenched by the addition of water (15 ml)
3. additionIce is added to the reaction mixture
4. stirringwhile stirring
5. customa yellow precipitate is formed
6. filtrationThis solid is collected by filtration
7. customto dry (60° C. for 16 hours)

ORDレコード

ord-014eeb49760a484c8dd708f60d857bb0

出典データセット

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08071776B2