Water → 3-(4-fluorophenyl)-3-methoxy-3-(5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-2H-[1,2,4]triazol-3-yl)propan-1-ol

HRID 1009408Notes

Reaction equation

HRID 1009408 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:16][CH3:17])([CH2:13][CH2:14][OH:15])[C:9]([NH:11][NH2:12])=O)=[CH:4][CH:3]=1.Cl.Cl.[CH3:20][O:21][C:22]1[CH:23]=[C:24](/[CH:34]=[CH:35]/[C:36](=[NH:40])OCC)[CH:25]=[CH:26][C:27]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1.C(OCC)(=O)C.O>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:16][CH3:17])([C:9]2[NH:11][N:12]=[C:36](/[CH:35]=[CH:34]/[C:24]3[CH:25]=[CH:26][C:27]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:22]([O:21][CH3:20])[CH:23]=3)[N:40]=2)[CH2:13][CH2:14][OH:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 66838954ethyl(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate dihydrochlorideHCID 670673452-(4-Fluorophenyl)-4-hydroxy-2-methoxybutyric acid hydrazide

Product 1

HCID 670672233-(4-fluorophenyl)-3-methoxy-3-(5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-2H-[1,2,4]triazol-3-yl)propan-1-olYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

A solution of 2-(4-fluorophenyl)-4-hydroxy-2-methoxybutyric acid hydrazide (40 mg) in ethanol (1.6 mL) was added to a solution of ethyl(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate dihydrochloride (65 mg) and TEA (0.12 mL) in ethanol (0.7 mL), and the reaction solution was stirred at 75° C. for two days. The reaction solution was left to cool to room temperature. Then, ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate-methanol system) to obtain 38 mg of the title compound. The property value of the compound is as follows.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. customthe organic layer was separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-ecfe4983b58c4cda9b6412cbe6b321f5
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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