Sodium Iodide → HCID 58001733, compound

Temperature

80 °C

A solution of 1,1-dimethylethyl (1-{2-hydroxy-3-[7-(methyloxy)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-yl]propyl}-4-piperidinyl)carbamate (301 mg, 0.694 mmol) in chloroform (10 ml) and triethylamine (0.24 ml, 1.735 mmol) at rt under argon was treated with methanesulfonic anhydride (242 mg, 1.388 mmol) and heated at reflux for 2 h. The reaction mixture was then evaporated and dissolved in acetonitrile (10 ml), treated with sodium iodide (520 mg, 3.47 mmol) and heated at 80° C. for 0.25 h. The mixture was then cooled, evaporated was then treated with water (200 ml), extracted with 20% methanol/DCM (3×200 ml). The organic extracts were dried (MgSO4), evaporated and chromatographed (0-10% methanol/DCM) to give the product as an orange oil (194 mg, 70%).

1. temperatureheated
2. temperatureat reflux for 2 h
3. customThe reaction mixture was then evaporated
4. dissolutiondissolved in acetonitrile (10 ml)
5. temperatureThe mixture was then cooled
6. customevaporated
7. additionwas then treated with water (200 ml)
8. extractionextracted with 20% methanol/DCM (3×200 ml)
9. dry with materialThe organic extracts were dried (MgSO4)
10. customevaporated
11. customchromatographed (0-10% methanol/DCM)

ORD record

ord-adbb2472c7e248c0baf58c5aff52064a

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389524B2