Sodium Iodide → 3-{4-[(2-Aminoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[(4-bromo-2-furyl)methyl]-1,2,4-oxadiazol-5(4H)-one hydroiodide

HRID 69810Notes

Reaction equation

HRID 69810 reaction equation
[N:1]([CH2:4][CH2:5][NH:6][C:7]1[C:8]([C:12]2[N:16]([CH2:17][C:18]3[O:19][CH:20]=[C:21]([Br:23])[CH:22]=3)[C:15](=[O:24])[O:14][N:13]=2)=[N:9][O:10][N:11]=1)=[N+]=[N-].[I-:25].[Na+].Cl[Si](C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO.O>[IH:25].[NH2:1][CH2:4][CH2:5][NH:6][C:7]1[C:8]([C:12]2[N:16]([CH2:17][C:18]3[O:19][CH:20]=[C:21]([Br:23])[CH:22]=3)[C:15](=[O:24])[O:14][N:13]=2)=[N:9][O:10][N:11]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium ThiosulfateHCID 86638029HCID 86638029, compound

Product 1

HCID 666060193-{4-[(2-Aminoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[(4-bromo-2-furyl)methyl]-1,2,4-oxadiazol-5(4H)-one hydroiodideYield 61.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-{4-[(2-azidoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[(4-bromo-2-furyl)methyl]-1,2,4-oxadiazol-5(4H)-one (7.7 g, 19 mmol) in methanol (80 mL) was added sodium iodide (17.4 g, 116 mmol). After stirring for 10 minutes, a solution of chlorotrimethylsilane (14.8 mL, 116 mmol) was added dropwise over 5 minutes. The reaction continued to stir for 1 hour, at which time it was slowly added to a solution of sodium thiosulfate (23.0 g, 145 mmol) in water (800 mL) at 0° C., resulting in a precipitate. The flask was rinsed with methanol (10 mL) and the precipitate was collected through vacuum filtration. The solid was rinsed with cold water (2×25 mL) and was dried under vacuum to give the desired product (5.8 g, 60%) as the hydroiodide salt. LCMS calculated for C11H12BrN6O4 (M+H)+: m/z=370.9, 372.8. 1H NMR (400 MHz, DMSO-d6): δ 7.86 (s, 1 H), 7.36 (br s, 3 H), 6.68 (t, J=5.8 Hz, 1 H), 6.65 (s, 1 H), 5.07 (s, 2 H), 3.45 (q, J=5.8 Hz, 2 H), 2.98 (t, J=5.8 Hz, 2 H).

Workup

  1. stirringto stir for 1 hour, at which time it
  2. customresulting in a precipitate
  3. washThe flask was rinsed with methanol (10 mL)
  4. filtrationthe precipitate was collected through vacuum filtration
  5. washThe solid was rinsed with cold water (2×25 mL)
  6. customwas dried under vacuum

Sources & evidence

ORD record
ord-a4958850e1ca4b3fb9ead05eecef9754
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Reaction notes

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