Sodium Azide → HCID 86616332, compound

HRID 1802599Notes

Reaction equation

HRID 1802599 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:16]=[CH:15][C:14]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])[CH:7]=1.[CH3:24][Si](C=[N+]=[N-])(C)C.[N-:31]=[N+:32]=[N-:33].[Na+].C([O-])(O)=O.[Na+]>CO.O=S(Cl)Cl.CN(C=O)C.CCOC(C)=O.O.O1CCOCC1>[N:31]([CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:16]=[CH:15][C:14]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])=[CH:13][C:9]=2[C:10]([O:12][CH3:24])=[O:11])[CH:7]=1)=[N+:32]=[N-:33]

Participants

11

Reactant 4

HCID 33557Sodium AzideHCID 167693Trimethylsilyldiazomethane2×HCID 516892Sodium BicarbonateHCID 66974111HCID 66974111, compound

Product 1

HCID 86616332HCID 86616332, compound

Reagents, catalysts & solvents 6

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(4-(hydroxymethyl)-1H-imidazol-1-yl)-5-(2-oxopyridin-1(2H)-yl)benzoic acid prepared above (92 mg, 0.30 mmol) in MeOH (4 mL) and dioxane (2 mL) at room temperature, (trimethylsilyl)diazomethane (2 M in ether, 0.30 mL, 0.60 mmol) was added. After the mixture was stirred at room temperature overnight, more (trimethylsilyl)diazomethane (2 M in ether, 0.40 mL, 0.80 mmol) was added. After stirring for another day, the solution was concentrated in vacuo to give a residue. The residue was dissolved in SOCl2 (4 mL). The solution was stirred at room temperature for 20 min before it was concentrated in vacuo to give a residue, which was then dissolved in DMF (3 mL). To the solution, NaN3 (65 mg, 1.0 mmol) was added. After the mixture was stirred at room temperature for 2 h, water and EtOAc were added, then 5% aq. NaHCO3 was added. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give methyl 2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-(2-oxopyridin-1(2H)-yl)benzoate (25 mg). MS 351.1 (M+H).

Workup

  1. stirringAfter stirring for another day
  2. concentrationthe solution was concentrated in vacuo
  3. customto give a residue
  4. stirringThe solution was stirred at room temperature for 20 min before it
  5. concentrationwas concentrated in vacuo
  6. customto give a residue, which
  7. stirringAfter the mixture was stirred at room temperature for 2 h
  8. customThe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-599346bb6c3f4206af6e75f3e346ca44
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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