HCID 14392115, compound → HCID 15615027, compound

To a stirred, refluxing solution of N,N-dimethyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-6-carboxamide (7.57 g, 0.0314 mol) under nitrogen in tetrahydrofuran (150 ml) was added dropwise over 10 minutes borane-dimethylsulfide complex (9.4 ml, 0.094 mol). Stirring at reflux was continued for 3 hours and 6NHCl (25 ml) was added dropwise and reflux was continued for 1/2 hour. Most of the tetrahydrofuran was removed in vacuo and the residue was diluted with 6NHCl (50 ml) and was heated for 1/2 hour at steam bath temperature under nitrogen. The mixture was cooled in ice and water (100 ml) was added to dissolve the solid, washed with ether (50 ml) and basified with 10H NaOH (75 ml). The product was extracted into ethyl acetate (200 ml) in four portions, washed with water and dried over Na2SO4. The solution was filtered and concentrated in vacuo to obtain an amber oil (5.7 g). Yield was 85%.

1. additionwas added dropwise over 10 minutes borane-dimethylsulfide complex (9.4 ml, 0.094 mol)
2. temperatureat reflux
3. addition6NHCl (25 ml) was added dropwise
4. temperaturereflux
5. waitwas continued for 1/2 hour
6. customMost of the tetrahydrofuran was removed in vacuo
7. additionthe residue was diluted with 6NHCl (50 ml)
8. temperaturewas heated for 1/2 hour at steam bath temperature under nitrogen
9. temperatureThe mixture was cooled in ice
10. additionwater (100 ml) was added
11. dissolutionto dissolve the solid
12. washwashed with ether (50 ml)
13. extractionThe product was extracted into ethyl acetate (200 ml) in four portions
14. washwashed with water
15. dry with materialdried over Na2SO4
16. filtrationThe solution was filtered
17. concentrationconcentrated in vacuo

ORD record

ord-bae8b6f07fe149559d120d60a1c610e5

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04797413