Dimethylformamide → HCID 86668145, compound

Temperature

0 °C

Oxalyl chloride (0.56 mL, 6.6 mmol) was added to anhydrous dichloromethane (50 mL), N,N-dimethylformamide (0.51 mL, 6.6 mmol) was added thereto at 0° C., and the mixture was stirred for 30 min at 0° C. To this reaction solution was added a mixture of 1-(1H-indol-5-yl)pyrazole-4-carboxylic acid ethyl ester (1.40 g, 5.47 mmol) obtained in Preparation 1 and dichloromethane (50 mL). The mixture was stirred under reflux for 1 h at room temperature, and the solvent was removed. Tetrahydrofuran (100 mL) and 20% aqueous ammonium acetate solution (100 mL) were added, which was then heated for 30 min while being stirred under reflux. After completion of the reaction, the reaction solution was cooled. Ethyl acetate was added and the mixture was washed with aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound.

1. additionwas added
2. additionTo this reaction solution was added
3. stirringThe mixture was stirred
4. temperatureunder reflux for 1 h at room temperature
5. customthe solvent was removed
6. additionTetrahydrofuran (100 mL) and 20% aqueous ammonium acetate solution (100 mL) were added
7. temperaturewhich was then heated for 30 min
8. stirringwhile being stirred
9. temperatureunder reflux
10. customAfter completion of the reaction
11. temperaturethe reaction solution was cooled
12. washthe mixture was washed with aqueous sodium hydrogen carbonate solution
13. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
14. concentrationconcentrated under reduced pressure

ORD record

ord-9aeb57bd17fd4a7196b8cacc65262202

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729273B2