Ammonia → HCID 24986862, compound

Trichloroacetyl isocyanate (0.10 mL, 0.85 mmol) was added to a solution of 2-amino-6-bromo-1-hydroxyindole-3-carboxamide (Reference compound 2-1, 180 mg, 0.71 mmol) in acetonitrile (5 mL), and the mixture was stirred at room temperature for 5 hours. 2.0 M Ammonia in methanol solution (4.5 mL, 9.0 mmol) was added thereto, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, 1 N hydrochloric acid (6 mL) and water (25 mL) was added to the residue and the whole was extracted with ethyl acetate (20 mL). The organic layer was washed with water (20 mL) and brine (20 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resultant solid was washed with diethyl ether (10 mL), and dried under reduced pressure to give the title compound (90 mg) as a slightly brown solid (yield 42%).

1. stirringthe mixture was stirred at room temperature for 18 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure, 1 N hydrochloric acid (6 mL) and water (25 mL)
3. additionwas added to the residue
4. extractionthe whole was extracted with ethyl acetate (20 mL)
5. washThe organic layer was washed with water (20 mL) and brine (20 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. customAfter the solvent was evaporated under reduced pressure
8. washthe resultant solid was washed with diethyl ether (10 mL)
9. customdried under reduced pressure

ORD record

ord-e94cd4c24e0b4797b772a570062403fe

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193237B2