Sodium Azide → 3-[4-(azidomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one

HRID 1845747Notes

Reaction equation

HRID 1845747 reaction equation
CS(O[CH2:6][C:7]1[C:11]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)[C:15](=[O:25])[O:14][N:13]=2)=[N:10][O:9][N:8]=1)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C>[N:26]([CH2:6][C:7]1[C:11]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)[C:15](=[O:25])[O:14][N:13]=2)=[N:10][O:9][N:8]=1)=[N+:27]=[N-:28]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 589418054-[4-(3-Chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-ylmethyl methanesulfonate

Product 1

HCID 589418163-[4-(azidomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-oneYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(3-Chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-ylmethyl methanesulfonate (400 mg, 1.02 mmol) was dissolved in anhydrous DMF (10 mL) followed by addition of sodium azide (133 mg, 2.04 mmol). Reaction was stirred for 3 hrs. Consumption of starting material was monitored by TLC and HPLC. The reaction mixture was added to a mixture of (400 μL) bromine/water and stirred for 10 min. DCM was added and the layers were separated. The combined organics were dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (225 mg, 65%). MF=C11H5ClFN7O3; LCMS calculated for C11H6ClFN7O3(M+H)+: m/z=338.020.

Workup

  1. customReaction
  2. customConsumption of starting material
  3. additionThe reaction mixture was added to a mixture of (400 μL) bromine/water
  4. stirringstirred for 10 min
  5. additionDCM was added
  6. customthe layers were separated
  7. dry with materialThe combined organics were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-e78af7ff828f4a3e904da10860e49799
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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