Dimethylformamide → HCID 55211232, compound

To a solution of 6-amino-nicotinonitrile (2.4 g, 20.15 mmol) in DMF (40 mL) was added a 1 M solution of NaHMDS (22.0 mL, 22.0 mmol) in THF followed by sulfamoyl chloride (3.0 mL, 27.9 mmol). The mixture was stirred overnight and was then diluted with 1 N aqueous sodium hydroxide and a mixture of ether-hexanes. The aqueous layer was separated. The organic layer was extracted with 1 N aqueous sodium hydroxide (2×30 mL). The combined aqueous layers were washed with ether (3×30 mL), made acidic with 1 N aqueous HCl and extracted with ethyl acetate (3×40 mL). The combined organic phases were washed with brine (3×30 mL), dried over magnesium sulfate, treated with activated carbon, filtered through diatomaceous earth and concentrated in vacuo. The solid was adsorbed onto silica gel and purified by silica gel chromatography eluting with a gradient of 10-50% ethyl acetate in hexanes (compound precipitated on the column but dissolved over time at high ethyl acetate concentration) to afford 6-(dimethylaminosulfonylamino)-3-cyanopyridine as a white solid

1. customThe aqueous layer was separated
2. extractionThe organic layer was extracted with 1 N aqueous sodium hydroxide (2×30 mL)
3. washThe combined aqueous layers were washed with ether (3×30 mL)
4. extractionextracted with ethyl acetate (3×40 mL)
5. washThe combined organic phases were washed with brine (3×30 mL)
6. dry with materialdried over magnesium sulfate
7. additiontreated with activated carbon
8. filtrationfiltered through diatomaceous earth
9. concentrationconcentrated in vacuo
10. custompurified by silica gel chromatography
11. washeluting with a gradient of 10-50% ethyl acetate in hexanes (compound
12. customprecipitated on the column
13. dissolutiondissolved over time at high ethyl acetate concentration)

ORD record

ord-b53928056e8d4bc78b8a7f5e94f439e2

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063065B2