Sodium Azide → 5-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2-({1-[3-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714709Notes

Reaction equation

HRID 714709 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[N-:13]=[N+:14]=[N-:15].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]([CH2:33][CH:34]([OH:39])[C:35]([F:38])([F:37])[F:36])[C:26](=[O:32])[N:27]([CH2:29][C:30]#[CH:31])[N:28]=2)=[CH:20][CH:19]=1>C(#N)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]([CH2:33][CH:34]([OH:39])[C:35]([F:37])([F:38])[F:36])[C:26](=[O:32])[N:27]([CH2:29][C:30]3[N:13]=[N:14][N:15]([CH2:6][C:5]4[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=4)[CH:31]=3)[N:28]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 866909095-(4-Chlorophenyl)-2-(prop-2-yn-1-yl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 866909325-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2-({1-[3-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 6342AcetonitrileSolvent

Procedure

29 mg (0.12 mmol) of 3-(trifluoromethyl)benzyl bromide were initially charged in 1 ml of acetonitrile, and 8 mg (0.12 mmol) of sodium azide were added. The mixture was stirred at RT for 1 h. 0.24 mg (0.012 mmol) of copper(II) acetate monohydrate and 50 mg (0.14 mmol) of the compound from Example 13A were then added. The resulting mixture was stirred at room temperature for 11 days. The reaction mixture was then filtered through a little silica gel, the product being eluted with about 10 ml of ethyl acetate, and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 52 mg (65% of theory) of the target compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 11 days
  2. filtrationThe reaction mixture was then filtered through a little silica gel
  3. washthe product being eluted with about 10 ml of ethyl acetate
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-b402b7c0f8ec44798cb93f67b9a84440
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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