Malononitrile → HCID 4737337, compound

Malononitrile B (0.66 g, 10 mmol) was dissolved in 20 ml DMSO. Cesium carbonate (4.87 g, 15 mmol) was added to the reaction mixture followed by addition of 2,3-dichloroquinoxaline (2.0 g, 10 mmol). The reaction mixture was stirred at room temperature overnight. The crude reaction mixture was diluted with 50 ml ethyl acetate and washed with 1N HCl (2×50 mL). the mixture was extracted with ethyl acetate (2×80 mL). The combined organic layer was washed with brine solution (2×50 mL). The organic layer was collected and the solvent was removed under reduced pressure to yield the crude product C 2-(3-chloroquinoxalin-2-yl)malononitrile (2.0 g) which was used in the next step without further purification. Compound C (0.22 g, 1 mmol) was transferred to a microwave vessel containing 1 ml butyl amine. The reaction mixture was subjected to microwave irradiation at 70° C. for 30 min. The resultant crude reaction mixture was purified using column chromatography to yield compound D as shown in Scheme 3 (0.20 g, 86% yield). ESI (m/z): 266 (M+H+).

1. customThe crude reaction mixture
2. washwashed with 1N HCl (2×50 mL)
3. extractionthe mixture was extracted with ethyl acetate (2×80 mL)
4. washThe combined organic layer was washed with brine solution (2×50 mL)
5. customThe organic layer was collected
6. customthe solvent was removed under reduced pressure

ORD record

ord-003c215fd40e4925b4dd2097b077a898

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045483B2