Water → HCID 22259294, compound

HRID 1610964Notes

Reaction equation

HRID 1610964 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[F:15][C:16]([F:51])([F:50])[C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]2[O:26][CH:27]=[C:28]([CH2:30][O:31][C:32]3[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH2:40][CH2:41][N:42]4[CH:46]=[CH:45][N:44]=[C:43]4[CH2:47][CH2:48][NH2:49])=[CH:34][CH:33]=3)[N:29]=2)=[CH:19][CH:18]=1.O>C1COCC1>[F:51][C:16]([F:50])([F:15])[C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]2[O:26][CH:27]=[C:28]([CH2:30][O:31][C:32]3[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH2:40][CH2:41][N:42]4[CH:46]=[CH:45][N:44]=[C:43]4[CH2:47][CH2:48][NH:49][C:8](=[O:10])[CH3:9])=[CH:34][CH:33]=3)[N:29]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22259339HCID 22259339, compound

Product 1

HCID 22259294HCID 22259294, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (137 μl) and acetic anhydride (74.0 μl) were added to a solution of 2-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]ethylamine (200 mg) in THF at 0° C., and the mixture was stirred at 0° C. for 1.5 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; dichloromethane to dichloromethane:methanol=20:1) and recrystallized from ethyl acetate-hexane to give the titled compound (123 mg) as colorless needle crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent; dichloromethane to dichloromethane:methanol=20:1)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-40aa6491d867428b82e6284b5351e73a
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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