Toluene → HCID 58012109, compound

HRID 660951Notes

Reaction equation

HRID 660951 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[C:12](=[O:13])[N:11]([CH2:14][C:15](=[O:28])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:10]=[C:9]1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)(C)(C)C.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:9]2[N:8]([CH2:7][C:6]([OH:36])=[O:5])[C:12](=[O:13])[N:11]([CH2:14][C:15](=[O:28])[NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=3)[N:10]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 58011780HCID 58011780, compound

Product 1

HCID 58012109HCID 58012109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

119 mg (0.23 mmol) of tert.-butyl[3-(4-chlorophenyl)-5-oxo-1-(2-oxo-2-{[3-(trifluoromethyl)-benzyl]amino}ethyl)-1,5-dihydro-4H-1,2,4-triazol-4-yl]-acetate from Example 420 are dissolved in 9 ml of dichloromethane and treated with 3 ml of trifluoroacetic acid. This is stirred for 24 hrs at RT. The reaction mixture is then treated with 10 ml of toluene and concentrated under reduced pressure. A further 10 ml of toluene are added, and the mixture again evaporated. This procedure is repeated once again. The crude product is then freed of solvent residues under high vacuum. 110 mg (quantitative) of the target compound are thus obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionA further 10 ml of toluene are added
  3. customthe mixture again evaporated
  4. custom110 mg (quantitative) of the target compound are thus obtained

Sources & evidence

ORD record
ord-50e5f242fd1d4bfbba079f7cdaeca8b1
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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