Sodium Iodide → HCID 58001733, compound

HRID 1943139Notes

Reaction equation

HRID 1943139 reaction equation
O[CH:2]([CH2:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:29]C)[N:27]=2)[CH2:22][CH2:21][C:20]1=[O:31])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[I-].[Na+]>C(Cl)(Cl)Cl>[O:29]=[C:26]1[CH:25]=[CH:24][C:23]2[CH2:22][CH2:21][C:20](=[O:31])[N:19]3[CH2:18][CH:2]([CH2:3][N:4]4[CH2:5][CH2:6][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:8][CH2:9]4)[N:27]1[C:28]=23

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 690465561,1-Dimethylethyl (1-{2-hydroxy-3-[7-(methyloxy)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-yl]propyl}-4-piperidinyl)carbamate

Product 1

HCID 58001733HCID 58001733, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-adbb2472c7e248c0baf58c5aff52064a
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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