Sodium Azide → HCID 89996210, compound

HRID 1480864Notes

Reaction equation

HRID 1480864 reaction equation
S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[CH3:16][O:17][C:18]1[N:23]=[C:22]([C:24]([NH:26][CH3:27])=O)[CH:21]=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29].[N-:31]=[N+:32]=[N-:33].[Na+].C([O-])(O)=O.[Na+]>CC#N>[CH3:16][O:17][C:18]1[C:19]([N+:28]([O-:30])=[O:29])=[CH:20][CH:21]=[C:22]([C:24]2[N:26]([CH3:27])[N:33]=[N:32][N:31]=2)[N:23]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 86726460HCID 86726460, compound

Product 1

HCID 89996210HCID 89996210, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triflic anhydride (0.29 mL, 1.724 mmol) was added dropwise to a solution of 6-methoxy-N-methyl-5-nitropicolinamide (Preparation 188, 0.182 g, 0.862 mmol) and sodium azide (0.224 g, 3.45 mmol) in MeCN (4.3 mL) at −10° C. The reaction mixture was warmed to room temperature over 3 hours. The reaction mixture was neutralised with saturated aqueous NaHCO3. The mixture was extracted with EtOAc and the organic layer washed with saturated aqueous NaHCO3 and then with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by Biotage silica gel column chromatography eluting with cyclohexane/EtOAc 70/30 to 50/50 to afford the title compound as a white solid (99 mg, 49%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organic layer washed with saturated aqueous NaHCO3
  3. dry with materialwith brine, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Biotage silica gel column chromatography
  7. washeluting with cyclohexane/EtOAc 70/30 to 50/50

Sources & evidence

ORD record
ord-af79bdc8cab643e4b6e1fe7b49995312
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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