Ethyl Acetate → 2-Methyl-6-nitro-2-[4-(4-trifluoromethylphenoxy)piperidin-1-ylmethyl]-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856247Notes

Reaction equation

HRID 856247 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][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].C(OCC)(=O)C>CN(C=O)C>[CH3:31][C:11]1([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[O:30][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 230811331-(2-Chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethylphenoxy)piperidin-1-yl]propan-2-ol

Product 1

HCID 104325792-Methyl-6-nitro-2-[4-(4-trifluoromethylphenoxy)piperidin-1-ylmethyl]-2,3-dihydroimidazo[2,1-b]oxazoleYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethylphenoxy)-piperidin-1-yl]propan-2-ol prepared in Example 230 (225 mg, 0.49 mmol) in DMF (2.5 ml), sodium hydride (23 mg, 0.59 mmol) was added followed by stirring for 1 hour with cooling on ice-bath. To the reaction mixture, ice-water and ethyl acetate were added. The precipitates were filtered off, washed with water, recrystallized from methylene chloride-diisopropyl ether and then washed with n-hexane to afford 2-methyl-6-nitro-2-[4-(4-trifluoromethylphenoxy)piperidin-1-ylmethyl]-2,3-dihydroimidazo[2,1-b]oxazole (80 mg, yield 39%) as a light yellow solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. filtrationThe precipitates were filtered off
  3. washwashed with water
  4. customrecrystallized from methylene chloride-diisopropyl ether
  5. washwashed with n-hexane

Sources & evidence

ORD record
ord-715ed10dc7194cbdb058297feb713548
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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