1H-1,2,4-Triazole → HCID 86751400, compound

HRID 1489443Notes

Reaction equation

HRID 1489443 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]([OH:36])([CH2:30]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][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])=[CH:18][CH:17]=2)[C:12]1=[O:29])[CH3:10].[NH:37]1[CH:41]=[N:40][CH:39]=[N:38]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:36])([CH2:30][N:37]1[CH:41]=[N:40][CH:39]=[N:38]1)[C@H:9]([N:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])=[CH:18][CH:17]=2)[C:12]1=[O:29])[CH3:10]

Participants

7

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 10697618HCID 10697618, compound

Product 1

HCID 86751400HCID 86751400, compoundYield 69%

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-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (3.6 g) was dissolved in 70 ml of dimethylformamide, to which 2.0 g of 1H-1,2,4-triazole and 7.8 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 150 ml of water, 1N-hydrochloric acid (100 ml×2) and 100 ml of an 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 (eluent; hexane:ethyl acetate=1:2 to ethyl acetate). The desired fraction was concentrated and the residue was recrystallized from diisopropyl ether to give 2.0 g of 1-[(1R,2S)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (yield: 69%) as a colorless powder.

Workup

  1. additionwere added
  2. washwashed with 150 ml of water, 1N-hydrochloric acid (100 ml×2) and 100 ml of an 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 (eluent; hexane:ethyl acetate=1:2 to ethyl acetate)
  6. concentrationThe desired fraction was concentrated
  7. customthe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ca3e415667ef4854be60c3caa5f3c1a6
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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