1-[Bis-(3-benzyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole → 1-[Bis-(3-hydroxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole

HRID 1685644Notes

Reaction equation

HRID 1685644 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:17]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31]CC3C=CC=CC=3)[CH:24]=2)[N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1>C1COCC1.CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:17]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([OH:31])[CH:24]=2)[N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

4

Reactant 1

HCID 587340101-[Bis-(3-benzyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole

Product 1

HCID 249016511-[Bis-(3-hydroxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

10% Pd/C (80 mg) was added to a solution of 1-[bis-(3-benzyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole (1.65 g, 3.25 mmol) in THF/MeOH (1:1, 200 mL). The solution was stirred under an atmosphere of H2 (provided by addition from a balloon) overnight. The excess H2 was removed and the reaction mixture was filtered through Celite® washing with THF and MeOH, then the solvent was removed in vacuo. The crude product was purified using Flashmaster II (EtOAc/Hexane) to give the title compound STX1003 (0.86 g, 81%, mp 217.5-219° C.) as a white solid; δH (270 MHz, d6-DMSO) 9.08 (2H, s, 2×OH), 8.47 (1H, s, NCHN), 8.03 (1H, s NCHN), 6.88 (2H, d, J=8.4, ArH), 6.76 (1H, s, CH), 6.64 (2H, s, ArH), 6.57 (2H, d, J=8.4, ArH), 3.74 (6H, s, 2×CH3); δC (68 MHz, d6-DMSO) 151.8 (CH), 147.3 (2×C), 146.3 (2×C), 144.0 (CH), 130.1 (2×C), 118.8 (2×CH), 115.3 (2×CH), 111.9 (2×CH), 64.9 (CH), 55.6 (2×Ch3); LCMS (ES−) 326.2 ([M−H]−, 100%), 255.9 (70), 240.4 (60), 211.4 (70); HRMS (FAB+) Found 327.1226, C17H17N3O4 requires 327.1219; HPLC (CH3CN/H2O, 90:10) tR=1.57 min 99+%); Found: C, 62.10%, H, 5.26%; N, 12.80%, C17H17N3O4 requires: C, 62.38%; H, 5.23%; N, 12.84%.

Workup

  1. customprovided by addition from a balloon) overnight
  2. customThe excess H2 was removed
  3. filtrationthe reaction mixture was filtered through Celite®
  4. washwashing with THF and MeOH
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-b97ed168b74a4755b2fcb9a96b3b9170
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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