4-[(4-Benzyloxy-3,5-dichloro-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile → 4-[(3,5-Dichloro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

HRID 901146Notes

Reaction equation

HRID 901146 reaction equation
C([O:8][C:9]1[C:29]([Cl:30])=[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[Cl:31])C1C=CC=CC=1>[Pd].CO.C1COCC1.CCOC(C)=O>[Cl:31][C:10]1[CH:11]=[C:12]([CH:28]=[C:29]([Cl:30])[C:9]=1[OH:8])[CH2:13][N:14]([N:23]1[CH:27]=[N:26][N:25]=[CH:24]1)[C:15]1[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 167495504-[(4-Benzyloxy-3,5-dichloro-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Product 1

HCID 167491184-[(3,5-Dichloro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19895526THF ethyl acetate methanolSolvent

Procedure

Palladium on charcoal (100 mg, 10% Pd) was added to a solution of 4-[(4-benzyloxy-3,5-dichloro-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02119, 1.13 g, 2.50 mmol) in MeOH/THF/EtOAc (30 mL/30 mL/40 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: 306 mg (34%). 1H-NMR (400 MHz, d6-DMSO) δ=4.97 (s, 2H, —CH2Ar), 6.76 (d, J=9.0 Hz, 2H), 7.31 (s, 2H), 7.77 (d, J=9.0 Hz, 2H), 8.85 (s, 2H), 10.29 (s, 1H, —OH). 13C-NMR (100 MHz, CDCl3) δ=56.57, 103.76, 114.55, 119.69, 122.89, 128.14, 129.46, 134.58, 144.03, 149.46, 151.85. LRMS (FAB+): 360.0 (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-edd9be648dd141e4aeb1dbf18836e220
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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