Sodium hydride → HCID 9910383, compound

HRID 856305Notes

Reaction equation

HRID 856305 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@@:11]([CH3:31])([OH:30])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>C1COCC1>[F:27][C:26]([F:29])([F:28])[O:25][C:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][C@:11]3([CH3:31])[O:30][C:2]4=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]4[CH2:10]3)[CH2:14][CH2:15]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 66589314HCID 66589314, compound

Product 1

HCID 9910383HCID 9910383, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethoxyphenyl)piperazin-1-yl]propan-2-ol prepared in Example 369 (5.85 g, 12.61 mmol) in THF (150 ml), sodium hydride (0.66 g, 18.92 mmol) was added with cooling on ice-bath followed by stirring under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added water and ethyl acetate. The precipitates were filtered off, purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) and recrystallized from isopropanol to afford (S)-2-[4-(4-trifluoromethoxyphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (2.58 g, yield 48%) as a light yellow solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was added water and ethyl acetate
  5. filtrationThe precipitates were filtered off
  6. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-f81ca37cbca9479ba25e21ca868e929d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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