Water → HCID 66589314, compound

HRID 856298Notes

Reaction equation

HRID 856298 reaction equation
[CH3:1][C@:2]1([CH2:5][N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:4][O:3]1.[Cl:23][C:24]1[NH:25][CH:26]=[C:27]([N+:29]([O-:31])=[O:30])[N:28]=1.C(=O)([O-])O.[Na+].O>C(#N)C>[Cl:23][C:24]1[N:25]([CH2:4][C@@:2]([CH3:1])([OH:3])[CH2:5][N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=3)[CH2:8][CH2:7]2)[CH:26]=[C:27]([N+:29]([O-:31])=[O:30])[N:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86604817HCID 86604817, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 66589314HCID 66589314, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (S)-1-(2-methyloxiran-2-ylmethyl)-4-(4-trifluoromethoxyphenyl)piperazine (0.43 g, 1.37 mmol) and 2-chloro-4-nitro-1H-imidazole (0.22 g, 1.51 mmol) in acetonitrile (4 ml), sodium hydrogencarbonate (0.17 g, 2.06 mmol) was added followed by stirring under reflux for 9 hours. To the reaction mixture, water was added, and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to afford (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethoxyphenyl)piperazin-1-yl]propan-2-ol (0.20 g, yield 31%) as a light yellow oil.

Workup

  1. additionwas added
  2. temperatureunder reflux for 9 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-f26dff3f6eac46a092afe1283e8910d6
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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