2-Mercaptoacetamide → HCID 22175936, compound

A solution (2 mL) of 2-mercaptoacetamide (0.27 g, 3.0 mmol) in N,N-dimethylformamide was ice-cooled under a nitrogen atmosphere and sodium hydride (0.12 g, 3.0 mmol) (60% in oil) was added thereto. The resulting mixture was stirred under ice-cooling for 30 min. To the obtained suspension was added 3-(aminomethyl)-6-bromo-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (1.06 g, 2.74 mmol), and the mixture was stirred at 80° C. for 24 h. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (50 mL), and the aqueous layer was extracted twice with ethyl acetate (50 mL). The extracts were combined and washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0–10:1 (v/v)) and recrystallized from n-hexane-ethyl acetate (1:1) to give the title compound (0.54 g, 50%) as a colorless powder.

1. temperaturecooled under a nitrogen atmosphere
2. temperaturecooling for 30 min
3. stirringthe mixture was stirred at 80° C. for 24 h
4. customThe reaction mixture was partitioned between water (100 mL) and ethyl acetate (50 mL)
5. extractionthe aqueous layer was extracted twice with ethyl acetate (50 mL)
6. washwashed with saturated brine (20 mL)
7. dry with materialdried over anhydrous magnesium sulfate (12 g)
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0–10:1 (v/v))
10. customrecrystallized from n-hexane-ethyl acetate (1:1)

ORD record

ord-548f52ae06484d91bedb393b1cafb390

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034039B2