4-[(4-Benzyloxy-3-trifluoromethyl-benzyl)-[1,2,4]triazol-4-yl-amino]benzonitrile → 4-[(4-Hydroxy-3-trifluoromethyl-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

HRID 19942Notes

Reaction equation

HRID 19942 reaction equation
C([O:8][C:9]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]([N:23]2[CH:27]=[N:26][N:25]=[CH:24]2)[C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:30]([F:33])([F:32])[F:31])C1C=CC=CC=1>[Pd].CCO.C1COCC1.CC#N>[OH:8][C:9]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]([N:23]2[CH:27]=[N:26][N:25]=[CH:24]2)[C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:30]([F:33])([F:32])[F:31]

Participants

4

Reactant 1

HCID 167495474-[(4-Benzyloxy-3-trifluoromethyl-benzyl)-[1,2,4]triazol-4-yl-amino]benzonitrile

Product 1

HCID 167491124-[(4-Hydroxy-3-trifluoromethyl-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86590896EtOH THF MeCNSolvent

Procedure

Palladium on charcoal (100 mg, 10% Pd) was added to a solution of 4-[(4-benzyloxy-3-trifluoromethyl-benzyl)-[1,2,4]triazol-4-yl-amino]benzonitrile (CAB03054, 1.75 g, 3.89 mmol) in EtOH/THF/MeCN (50 mL/50 mL/30 mL). The mixture was stirred under hydrogen atmosphere (balloon) for 18 h at room temperature. The reaction mixture was filtered through celite and the clear colourless filtrate was concentrated under reduced pressure. The residue was suspended in 2-propanol (20 mL) and heated to reflux for 5 minutes. The white solid was filtered off after cooling to room temperature and dried under high vacuum. Yield: 1.31 g (94%). 1H-NMR (400. MHz, d6-DMSO) δ=4.98 (s, 2H), 6.78 (4, J=9.0 Hz, 2H), 6.91 (d, J=8.6 Hz, 1H), 7.31 (dd, J=8.6, 2.0 Hz, 1H), 7.39 (d, J=2.0 Hz, 1H), 7.76 (d, J=9.0 Hz, 2H), 8.74 (s, 2H), 10.66 (s, 1H, —OH). LRMS (FAB+): 360.2 (100, [M+H]+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe clear colourless filtrate was concentrated under reduced pressure
  3. temperatureheated
  4. temperatureto reflux for 5 minutes
  5. filtrationThe white solid was filtered off
  6. temperatureafter cooling to room temperature
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-6451f7f844ea4ab4be63cc64a226dc59
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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