Water → HCID 69481303, compound

HRID 856253Notes

Reaction equation

HRID 856253 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)=[CH:6][CH:5]=1.Cl[C:19]1[N:20]([CH2:27][C@:28]2([CH3:31])[CH2:30][O:29]2)[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[N:23]=1.O.[H-].[Na+]>CN(C=O)C>[CH3:30][C@@:28]1([CH2:31][N:13]2[CH2:12][CH:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:16])[F:17])=[CH:5][CH:6]=3)[CH2:15][CH2:14]2)[O:29][C:19]2=[N:23][C:22]([N+:24]([O-:26])=[O:25])=[CH:21][N:20]2[CH2:27]1

Participants

6

Reactant 4

HCID 962Water2×HCID 24758Sodium hydrideHCID 10443353(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 23081382HCID 23081382, compound

Product 1

HCID 69481303HCID 69481303, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

4-(4-Trifluoromethoxyphenyl)-1,2,3,6-tetrahydropyridine (0.985 g, 4.05 mmol) and (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (0.839 g, 3.86 mmol) were added to DMF (15 ml), and the solution was stirred at 60° C. for 8 hours. The reaction mixture was added water and extracted with ethyl acetate. The organic phases was washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to afford as oil. The oil was dissolved in DMF (20 ml), and sodium hydride (94 mg, 2.35 mmol) was added with cooling on ice-bath followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to afford (S)-2-methyl-6-nitro-2-[4-(4-trifluoromethoxyphenyl)-1,2,3,6-tetrahydropyridin-1-ylmethyl]-2,3-dihydroimidazo[2,1-b]oxazole (0.192 g, yield 23%) as a light yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases was washed with water
  3. dry with materiala saturated saline solution, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe resulting filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)
  7. customto afford as oil
  8. temperaturewith cooling on ice-bath
  9. stirringby stirring at room temperature overnight
  10. extractionthe solution was extracted with ethyl acetate
  11. washThe organic phase was washed with water
  12. dry with materiala saturated saline solution, dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationThe resulting filtrate was concentrated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-b7c2fc01c2b749e89810681945cda968
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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