1H-1,2,4-Triazole → HCID 86751399, compound

HRID 1489440Notes

Reaction equation

HRID 1489440 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]([OH:37])([CH2:31]OS(C)(=O)=O)[C@H:9]([N:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[CH:18][CH:17]=2)[C:12]1=[O:30])[CH3:10].[NH:38]1[CH:42]=[N:41][CH:40]=[N:39]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.C(OC(C)C)(C)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]([OH:37])([CH2:31][N:38]1[CH:42]=[N:41][CH:40]=[N:39]1)[C@H:9]([N:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:26])[F:27])=[CH:18][CH:17]=2)[C:12]1=[O:30])[CH3:10]

Participants

7

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 10602738HCID 10602738, compound

Product 1

HCID 86751399HCID 86751399, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 7914Diisopropyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-[(1R,2S)-2-(2-Fluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (2.2 g) was dissolved in 40 ml of dimethylformamide, to which 1.39 g of 1H-1,2,4-triazole and 5.55 g of potassium carbonate were added. The mixture was heated at 80° C. for 4 hours. The reaction solution was diluted with a mixture of 150 ml of ethyl acetate and 50 ml of diisopropyl ether, and washed with water (40 ml×2), 1N-hydrochloric acid (40 ml×2) and 20 ml of aqueous solution of sodium chloride successively. The organic layer was dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography (silica gel: 50 g, eluent; hexane:ethyl acetate=1:1 to 1:2). The desired fraction was concentrated and the residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 1.59 g of 1-[(1R,2S)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (yield: 75%) as colorless powdery crystals.

Workup

  1. additionwere added
  2. washwashed with water (40 ml×2), 1N-hydrochloric acid (40 ml×2) and 20 ml of aqueous solution of sodium chloride successively
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel chromatography (silica gel: 50 g, eluent; hexane:ethyl acetate=1:1 to 1:2)
  6. concentrationThe desired fraction was concentrated
  7. customthe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-86160ecf5ba14793baa2e22db21a357b
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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