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

HRID 415812Notes

Reaction equation

HRID 415812 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Br:25])[CH:19]=3)[C:16](=[O:26])[O:15][N:14]=2)=[N:10][O:11][N:12]=1)=[N+]=[N-].[I-:27].[Na+].Cl[Si](C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO.O>[IH:27].[NH2:1][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Br:25])[CH:19]=3)[C:16](=[O:26])[O:15][N:14]=2)=[N:10][O:11][N:12]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium ThiosulfateHCID 866380023-{4-[(3-azidopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 666058273-{4-[(3-Aminopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodideYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-{4-[(3-azidopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (2.0 g, 4.7 mmol) in methanol (36 mL) was treated with sodium iodide (4.2 g, 28 mmol) and stirred at 25° C. for 5 min. The reaction mixture was treated with a solution of chlorotrimethylsilane (3.6 mL, 28 mmol) in methanol (7 mL) dropwise and stirred at 25° C. for 40 min. The reaction mixture was slowly poured into a solution of sodium thiosulfate (5.0 g, 32 mmol) in water (200 mL) that was cooled at 0° C. The solid that precipitated was filtered, washed with water, and dried to give the desired product (2.3 g, 93%) as a solid. LCMS for C13H13BrFN6O3 (M+H)+: m/z=399.0, 401.0. 1H NMR (400 MHz, DMSO-d6): δ 8.08 (dd, J=6.1, 2.3 Hz, 1H), 7.74-7.70 (m, 1H), 7.60 (dd, J=8.8, 8.6 Hz, 1H), 7.22 (br s, 2H), 6.69 (br s, 1H), 2.81-2.77 (m, 2H), 1.86-1.79 (m, 2H).

Workup

  1. stirringstirred at 25° C. for 40 min
  2. temperaturewas cooled at 0° C
  3. customThe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ac5479671d624355a05c605183afe732
Source dataset
uspto-grants-2012_01
Patent number
US08088803B2

Reaction notes

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