Ethyl Acetate → 5-(4-Chlorophenyl)-4-cyclopropyl-2-({4-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}-methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714716Notes

Reaction equation

HRID 714716 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[N:6]([CH:9]2[CH2:11][CH2:10]2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[N:4]1.[N-:19]=[N+:20]=[N-:21].[Na+].[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([F:34])([F:33])[F:32])#[CH:24].C(OCC)(=O)C>C(#N)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[N:6]([CH:9]3[CH2:11][CH2:10]3)[C:7](=[O:8])[N:3]([CH2:2][N:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:32])([F:33])[F:34])[N:21]=[N:20]3)[N:4]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 41008561-Ethynyl-2-(trifluoromethyl)benzeneHCID 674116472-(Chloromethyl)-5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 699403765-(4-Chlorophenyl)-4-cyclopropyl-2-({4-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}-methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 6342AcetonitrileSolvent

Procedure

60 mg (0.21 mmol) of the compound from Example 122A were dissolved in 2 ml of acetonitrile, 14 mg (0.21 mmol) of sodium azide were added and the mixture was stirred at RT for 1 h. 0.4 mg (0.002 mmol) of copper(II) acetate monohydrate and 43 mg (0.25 mmol) of 1-ethynyl-2-(trifluoro-methyl)benzene were then added. The resulting mixture was stirred at RT for 20 h. For work-up, 10 ml of ethyl acetate were added and the mixture was washed twice with in each case 5 ml of water. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 48 mg (45% of theory) of the target compound.

Workup

  1. stirringThe resulting mixture was stirred at RT for 20 h
  2. washthe mixture was washed twice with in each case 5 ml of water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-65855bc6aedf41f88f4a5b2e21ce0b19
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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