HCID 21976895, compound → 4-[(3-Fluoro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

HRID 901167Notes

Reaction equation

HRID 901167 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[F:30])C1C=CC=CC=1>C(O)C.C1COCC1.C(OCC)(=O)C.[Pd]>[F:30][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][C:9]=1[OH:8])[CH2:13][N:14]([N:23]1[CH:24]=[N:25][N:26]=[CH:27]1)[C:15]1[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=1

Participants

6

Reactant 1

HCID 21976895HCID 21976895, compound

Product 1

HCID 219769034-[(3-Fluoro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[(4-Benzyloxy-3-fluoro-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB033019, 2.83 g, 7.09 mmol) was dissolved in a mixture of ethanol (50 mL), THF (50 mL) and ethyl acetate (50 mL) by heating and palladium on charcoal (150 mg, 5% Pd) was added. The mixture was stirred under hydrogen-atmosphere (balloon) for 18 h, filtered through a 3 cm layer of celite and concentrated under reduced pressure. The residue was suspended in 2-propanol (30 mL), the mixture was heated to reflux for 5 minutes. After cooling room temperature the white precipitate was filtered off and dried under high vacuum. Yield: 2.13 g (97%). 1H-NMR (400 MHz, d6-DMSO) δ=4.93 (s, 2H), 6.75 (d, J=9.0 Hz, 2H), 6.82-6.89 (m, 2H), 7.07-7.12 (m, 1H), 7.76 (d, J=9.0 Hz, 2H), 8.77 (s, 2H), 9.95 (s, 1H, —OH).

Workup

  1. temperatureby heating
  2. filtrationfiltered through a 3 cm layer of celite and
  3. concentrationconcentrated under reduced pressure
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 5 minutes
  6. filtrationwas filtered off
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-f399f12bc4f34f8d8dfad07ed47f2929
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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