2,5-Dimethoxytetrahydrofuran → 2-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

HRID 351260Notes

Reaction equation

HRID 351260 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[N:16]=[C:15]([C:25]([F:28])([F:27])[F:26])[CH:14]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].CO[CH:31]1[CH2:35][CH2:34][CH:33](OC)O1>CC(O)=O>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH:31]=[CH:35][CH:34]=[CH:33]4)=[CH:20][CH:19]=3)[N:16]=[C:15]([C:25]([F:26])([F:28])[F:27])[CH:14]=2)=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 790982,5-Dimethoxytetrahydrofuran2×HCID 210907062-{4-[1-(4-aminophenyl)-3-(trifluoro-methyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

Product 1

HCID 210907052-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetateYield 72.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-{4-[1-(4-aminophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate 165.6 mg and 2,5-dimethoxytetrahydrofuran 112 mg in AcOH 3 ml was stirred at 50° C. for 3 hours. 2,5-Dimethoxytetrahydrofuran 0.22 ml was added and the mixture was stirred at 50° C. for 2 hours. The mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by AcOEt/n-hexane=20%. The separated silica gel was extracted with 10% MeOH/CHCl3 and the solvent was evaporated in vacuo to give 2-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate 136.1 mg as an oil.

Workup

  1. stirringthe mixture was stirred at 50° C. for 2 hours
  2. customThe mixture was partitioned between ethyl acetate and H2O
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer silica gel chromatography
  7. extractionThe separated silica gel was extracted with 10% MeOH/CHCl3
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fee74556b62b4488bade5b3d017dce4f
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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