1-Azido-2,3-dichlorobenzene → 5-(4-Chlorophenyl)-2-{[1-(2,3-dichlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714711Notes

Reaction equation

HRID 714711 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:17][C@H:18]([OH:23])[C:19]([F:22])([F:21])[F:20])[C:10](=[O:16])[N:11]([CH2:13][C:14]#[CH:15])[N:12]=2)=[CH:4][CH:3]=1.[N:24]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=1[Cl:34])=[N+:25]=[N-:26]>C(#N)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:17][C@H:18]([OH:23])[C:19]([F:21])([F:22])[F:20])[C:10](=[O:16])[N:11]([CH2:13][C:14]3[N:26]=[N:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=4[Cl:34])[CH:15]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 126814021-Azido-2,3-dichlorobenzeneHCID 866909105-(4-Chlorophenyl)-2-(prop-2-yn-1-yl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 866909345-(4-Chlorophenyl)-2-{[1-(2,3-dichlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

124 mg (0.36 mmol) of the compound from Example 14A were dissolved in 2 ml of acetonitrile, and 0.6 mg (0.003 mmol) of copper(II) acetate monohydrate and 56 mg (0.30 mmol) of 1-azido-2,3-dichlorobenzene were added. The mixture was stirred at 50° C. for 2 h. For work-up, the crude mixture was allowed to cool to RT and filtered through a little silica gel. The product was eluted with ethyl acetate and the solution obtained was concentrated under reduced pressure. The crude product was then purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). This gave 61 mg (31% of theory) of the target compound.

Workup

  1. temperatureto cool to RT
  2. filtrationfiltered through a little silica gel
  3. washThe product was eluted with ethyl acetate
  4. customthe solution obtained
  5. concentrationwas concentrated under reduced pressure
  6. customThe crude product was then purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-35728875fa3d49d8bb32f9a35f664351
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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