5-(3-benzyloxy-4-methoxy-phenyl)-3-(3-pyrrolidin-1-ylmethyl-phenyl)-1H-[1,2,4]triazole hydrochloride → 2-Methoxy-5-[5-(3-pyrrolidin-1-ylmethyl-phenyl)-2H-[1,2,4]triazol-3-yl]-phenol hydrochloride

HRID 1386928Notes

Reaction equation

HRID 1386928 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[C:12]([C:18]2[NH:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[CH:24]=3)[N:19]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])C1C=CC=CC=1>C(O)C.[Pd]>[ClH:1].[CH3:17][O:16][C:15]1[CH:14]=[CH:13][C:12]([C:18]2[NH:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[CH:24]=3)[N:19]=2)=[CH:11][C:10]=1[OH:9]

Participants

4

Reactant 1

HCID 211803505-(3-benzyloxy-4-methoxy-phenyl)-3-(3-pyrrolidin-1-ylmethyl-phenyl)-1H-[1,2,4]triazole hydrochloride

Product 1

HCID 211802732-Methoxy-5-[5-(3-pyrrolidin-1-ylmethyl-phenyl)-2H-[1,2,4]triazol-3-yl]-phenol hydrochlorideYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-(3-benzyloxy-4-methoxy-phenyl)-3-(3-pyrrolidin-1-ylmethyl-phenyl)-1H-[1,2,4]triazole hydrochloride (1:1) (300 mg, 0.63 mmol) in ethanol (80 ml) was hydrogenated (1 atm H2) with Pd/C (10%, 50 mg) at 20° C. overnight. The catalyst was filtered off, the solvent volume was reduced to ca. 5 ml and the resulting product recrystallized. After drying under high vaccum at 40° C. for 8 hrs. the title compound was obtained (152 mg, 63% yield) as a light yellow solid. MS: m/e=351.4 (M+H+).

Workup

  1. customat 20° C.
  2. customovernight
  3. filtrationThe catalyst was filtered off
  4. customthe resulting product recrystallized
  5. customAfter drying under high vaccum at 40° C. for 8 hrs

Sources & evidence

ORD record
ord-dcd247ccb28b453c9926977d56378e97
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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