Sodium Iodide → HCID 23081361, compound

HRID 856351Notes

Reaction equation

HRID 856351 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:11][C:10](=[O:12])[NH:9][N:8]=2)=[CH:3][CH:2]=1.[H-].[Na+].CS(O[CH2:20][CH2:21][C:22]1([CH3:33])[O:26][C:25]2=[N:27][C:28]([N+:30]([O-:32])=[O:31])=[CH:29][N:24]2[CH2:23]1)(=O)=O.[I-].[Na+]>O.CN(C=O)C>[CH3:33][C:22]1([CH2:21][CH2:20][N:9]2[N:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[O:11][C:10]2=[O:12])[O:26][C:25]2=[N:27][C:28]([N+:30]([O-:32])=[O:31])=[CH:29][N:24]2[CH2:23]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 3129241,3,4-Oxadiazol-2-ol, 5-(4-pyridinyl)-HCID 230810922-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl methanesulfonate

Product 1

HCID 23081361HCID 23081361, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(pyridin-4-yl)-3H-[1,3,4]-oxadiazol-2-one (150 mg, 0.92 mmol), sodium hydride (41 mg, 1.03 mmol) and DMF (1.5 ml) was stirred at room temperature for 1 hour. To the reaction mixture, 2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl methanesulfonate prepared in Example 42 (200 mg, 0.69 mmol) and sodium iodide (140 mg, 0.93 mmol) were added in this order followed by stirring at 50-60° C. for 6 hours. The reaction mixture was allowed to return to room temperature. To the solution, water was added, and the resulting solution was extracted with ethyl acetate twice. The organic phases were combined, washed with water three times, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=25/1) to afford 3-[2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl]-5-(pyridin-4-yl)-3H-[1,3,4]oxadiazol-2-one (137 mg, yield 56%) as a white powder.

Workup

  1. stirringby stirring at 50-60° C. for 6 hours
  2. customto return to room temperature
  3. extractionthe resulting solution was extracted with ethyl acetate twice
  4. washwashed with water three times
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=25/1)

Sources & evidence

ORD record
ord-8554b910a92443aab2f55d1b8b73c9f2
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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