Water → 3-{4-[(2-Azidoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5(4H)-one

HRID 69791Notes

Reaction equation

HRID 69791 reaction equation
CS(O[CH2:6][CH2:7][NH:8][C:9]1[C:13]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:17](=[O:29])[O:16][N:15]=2)=[N:12][O:11][N:10]=1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+].O>CN(C)C=O>[N:30]([CH2:6][CH2:7][NH:8][C:9]1[C:13]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:17](=[O:29])[O:16][N:15]=2)=[N:12][O:11][N:10]=1)=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86638017HCID 86638017, compound

Product 1

HCID 866380183-{4-[(2-Azidoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5(4H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[(4-{5-Oxo-4-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2,4-oxadiazol-3-yl}-1,2,5-oxadiazol-3-yl)amino]ethyl methanesulfonate (1.2 g, 2.9 mmol) was dissolved in N,N-dimethylformamide (2.7 mL). After sodium azide (280 mg, 4.3 mmol) was added in one portion, the temperature was brought to 65° C. and the reaction stirred for 6 hours. After cooling back to room temperature, water (10 mL) was added to quench the reaction. The product was extracted with ethyl acetate (3×10 mL) and the combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo to give the desired product (1.05 g, 96%). LCMS calculated for C13H10F3N6O3 (M-N2+H)+: m/z=355.0. 1H NMR (400 MHz, DMSO-d6): δ 8.09 (s, 1H), 7.93 (m, 2H), 7.79 (t, J=8.2 Hz, 1H), 6.75 (t, J=5.8 Hz, 1H), 3.52 (t, J=5.7 Hz, 2H), 3.44 (q, J=5.5 Hz, 2H).

Workup

  1. customwas brought to 65° C.
  2. customto quench
  3. customthe reaction
  4. extractionThe product was extracted with ethyl acetate (3×10 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-449969ab30874fe3a1d9b9c511f7bc53
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Reaction notes

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