Imidazole → HCID 15337562, compound

HRID 2397008Notes

Reaction equation

HRID 2397008 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C@:16]1([C@H:19]([N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)[CH3:20])[CH2:18][O:17]1.O>CN(C)C=O.C(OCC)(=O)C>[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C@:16]([OH:17])([C@H:19]([N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)[CH3:20])[CH2:18][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 15337561HCID 15337561, compound

Product 1

HCID 15337562HCID 15337562, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In dimethylformamide (2 ml) was dispersed 60% sodium hydride in oil (52 mg). Imidazole (89 mg) was added to the dispersion under ice-cooling and the mixture was stirred for 15 minutes at room temperature. To the mixture was added a solution of (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(1H-pyrazol-1-yl)ethyl]oxirane (166 mg) in dimethylformamide (1 ml). The mixture was heated for 5 hours at 50° C. and cooled. To the reaction mixture were added cold water (5 ml) and ethyl acetate (30 ml). The separated aqueous layer was extracted twice with ethyl acetate. The combined ethyl acetate layers were washed with water and saturated saline, dried over magnesium sulfate and distilled under reduced pressure. The residue was allowed to stand to crystallize. The obtained crystals were recrystallized from ethyl acetate-hexane to form the title compound (Compound 1, 193 mg) as colorless prisms.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated for 5 hours at 50° C.
  3. temperaturecooled
  4. extractionThe separated aqueous layer was extracted twice with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water and saturated saline
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto crystallize
  9. customThe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6731eca81c514ac7822fb1c5eadf0143
Source dataset
uspto-grants-1996_02
Patent number
US05495024

Reaction notes

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