Dimethylformamide → HCID 86668146, compound

Temperature

0 °C

To anhydrous dichloromethane (30 mL) was added oxalyl chloride (0.03 mL, 0.36 mmol). N,N-dimethylformamide (0.03 mL, 0.36 mmol) was added at 0° C., which was then stirred for 30 min at 0° C. To this solution was added 1-(1-isopropylindol-5-yl)-imidazole-4-carboxylic acid ethyl ester (0.09 g, 0.3 mmol) obtained in Preparation 27, and the mixture was stirred for 1 h at room temperature. The solvent was removed, tetrahydrofuran (30 mL) and 20% aqueous ammonium acetate solution (30 mL) were added to the residue, and the mixture was heated for 30 min while being stirred under reflux. The reaction solution was cooled, ethyl acetate was added, and washed with aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was filtered, washed with ethyl acetate and dried to give the title compound (0.09 g, 92% Yield).

1. customobtained in Preparation 27
2. stirringthe mixture was stirred for 1 h at room temperature
3. customThe solvent was removed
4. additiontetrahydrofuran (30 mL) and 20% aqueous ammonium acetate solution (30 mL) were added to the residue
5. temperaturethe mixture was heated for 30 min
6. stirringwhile being stirred
7. temperatureunder reflux
8. temperatureThe reaction solution was cooled
9. additionethyl acetate was added
10. washwashed with aqueous sodium bicarbonate solution
11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
12. concentrationconcentrated under reduced pressure
13. filtrationThe resulting solid was filtered
14. washwashed with ethyl acetate
15. customdried

ORD record

ord-d0b0b4f4019f42fbaabf8633841ce9e3

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729273B2