Ethyl Acetate → HCID 178489883, compound

HRID 1009361Notes

Reaction equation

HRID 1009361 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][NH:11][C:12](=O)/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]3)=[C:17]([O:27][CH3:28])[CH:16]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:35].C(OCC)(=O)C.O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:35]=[C:12](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]4)=[C:17]([O:27][CH3:28])[CH:16]=3)[NH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 67067457HCID 67067457, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 178489883HCID 178489883, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7237O-XyleneSolvent

Procedure

A solution of (E)-N-[3-(4-fluorophenyl)-2-oxopropyl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide (43 mg) and ammonium acetate (163 mg) in acetic acid (1 mL) and xylene (5 mL) was heated under reflux for 16 hours. The reaction solution was left to cool to room temperature. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 13 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperatureunder reflux for 16 hours
  2. waitThe reaction solution was left
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-3e4732be065f41089d4629aa2e6e33c9
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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