Ethyl Acetate → 2-{(Z)-1-fluoro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine

HRID 546674Notes

Reaction equation

HRID 546674 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:15]1O[C:17](/[C:20](/[F:36])=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]3)=[C:24]([O:34][CH3:35])[CH:23]=2)=[N:18][N:19]=1)[C:6]1[CH:11]=[C:10]([F:12])[C:9]([F:13])=[C:8]([F:14])[CH:7]=1.C([O-])(=O)C.[NH4+:41].C(OCC)(=O)C.O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[F:36]/[C:20](/[C:17]1[N:41]=[C:15]2[CH:5]([C:6]3[CH:11]=[C:10]([F:12])[C:9]([F:13])=[C:8]([F:14])[CH:7]=3)[CH2:4][CH2:3][CH2:2][N:19]2[N:18]=1)=[CH:21]\[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]2)=[C:24]([O:34][CH3:35])[CH:23]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 668393462-[4-chloro-1-(3,4,5-trifluorophenyl)butyl]-5-{(Z)-1-fluoro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazoleHCID 86585896Sodium bicarbonate water

Product 1

HCID 248530042-{(Z)-1-fluoro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridineYield 130.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-[4-chloro-1-(3,4,5-trifluorophenyl)butyl]-5-{(Z)-1-fluoro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazole (81 mg) and ammonium acetate (358 mg) in acetic acid (2 mL) was stirred at 150° C. for three hours. The reaction solution was left to cool to room temperature. Then, 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: heptane:ethyl acetate=1:1→ethyl acetate) to obtain 98 mg of the title compound. The property values of the compound are as follows.

Workup

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

Sources & evidence

ORD record
ord-9bb75ab5863c46cc988b65a78bfebd97
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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