Dimethylformamide → 4-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

HRID 546730Notes

Reaction equation

HRID 546730 reaction equation
CN(C=O)C.[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[NH:18][C:17](/[CH:19]=[CH:20]/[C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]4)=[C:23]([O:33][CH3:34])[CH:22]=3)=[N:16][N:15]=2)=[CH:9][CH:8]=1.[C:35](Cl)(=[O:38])[CH:36]=[CH2:37]>C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:35](=[O:38])[CH2:36][CH2:37][N:15]3[N:16]=[C:17](/[CH:19]=[CH:20]/[C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]5)=[C:23]([O:33][CH3:34])[CH:22]=4)[N:18]=[C:14]23)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 13140Acryloyl chloride2×HCID 178489930HCID 178489930, compound

Product 1

HCID 576092174-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

DMF (3 mL) and TEA (0.06 mL) were added to (4-fluorophenyl)-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-4H-[1,2,4]triazol-3-yl}amine synthesized in Example 162 (44 mg), and the reaction solution was stirred at room temperature for 10 minutes. Acrylic acid chloride (0.01 mL) was added to the reaction solution at room temperature, and the reaction solution was stirred at room temperature for one hour and at 60° C. for two hours. TEA (0.03 mL) and acrylic acid chloride (0.01 mL) were added to the reaction solution at 60° C., and the reaction solution was stirred at 60° C. for four hours. The reaction solution was left to cool to room temperature and then diluted with ethyl acetate and washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) and further purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 6 mg of the title compound. The property values of the compound are as follows.

Workup

  1. stirringthe reaction solution was stirred at room temperature for one hour and at 60° C. for two hours
  2. stirringthe reaction solution was stirred at 60° C. for four hours
  3. waitThe reaction solution was left
  4. temperatureto cool to room temperature
  5. washwashed with a saturated sodium bicarbonate solution
  6. dry with materialThe resulting organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (carrier
  9. washelution solvent
  10. customheptane-ethyl acetate system, then ethyl acetate-methanol system) and further purified by silica gel column chromatography (
  11. washelution solvent

Sources & evidence

ORD record
ord-a8e566c841b64dfca283123ef2e7b957
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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