Water → HCID 86638029, compound

HRID 2402248Notes

Reaction equation

HRID 2402248 reaction equation
CS(O[CH2:6][CH2:7][NH:8][C:9]1[C:13]([C:14]2[N:18]([CH2:19][C:20]3[O:21][CH:22]=[C:23]([Br:25])[CH:24]=3)[C:17](=[O:26])[O:16][N:15]=2)=[N:12][O:11][N:10]=1)(=O)=O.[N-:27]=[N+:28]=[N-:29].[Na+].O>CN(C)C=O>[N:27]([CH2:6][CH2:7][NH:8][C:9]1[C:13]([C:14]2[N:18]([CH2:19][C:20]3[O:21][CH:22]=[C:23]([Br:25])[CH:24]=3)[C:17](=[O:26])[O:16][N:15]=2)=[N:12][O:11][N:10]=1)=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 866380282-[(4-{4-[(4-Bromo-2-furyl)methyl]-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl}-1,2,5-oxadiazol-3-yl)amino]ethyl methanesulfonate

Product 1

HCID 86638029HCID 86638029, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[(4-{4-[(4-Bromo-2-furyl)methyl]-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl}-1,2,5-oxadiazol-3-yl)amino]ethyl methanesulfonate (9.1 g, 20 mmol, containing also some of the corresponding bromo-compound) was dissolved in dimethylformamide (90 mL). Sodium azide (1.97 g, 30.3 mmol) was added in one portion and after 5 minutes, the temperature was brought to 65° C. The reaction stirred for 2 hours and was allowed to cool back to room temperature. Water (200 mL) was added to quench the reaction. The product was extracted with ethyl acetate (3×100 mL) and the combined organic layers were washed with brine (2×150 mL) and water (150 mL). After drying over sodium sulfate, the solvent was removed in vacuo to give the desired product (7.7 g, 96%). LCMS calculated for C11H9BrN8NaO4 (M+Na)+: m/z=418.7, 421.0. 1H NMR (400 MHz, DMSO-d6): δ 7.88 (s, 1H), 6.71 (t, J=5.7 Hz, 1H), 6.68 (s, 1H), 5.08 (s, 2H), 3.54 (t, J=5.7 Hz, 2H), 3.47 (q, J=5.7 Hz, 2H).

Workup

  1. customwas brought to 65° C
  2. customto quench
  3. customthe reaction
  4. extractionThe product was extracted with ethyl acetate (3×100 mL)
  5. washthe combined organic layers were washed with brine (2×150 mL) and water (150 mL)
  6. dry with materialAfter drying over sodium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0bbcb4d0928841559ea4cc0dcca3911a
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

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