Hydrazine hydrate (1:1) → 4-[5-(4-fluorobenzyl)-1H-pyrazol-3-yl]-1-(4-methoxybenzyl)-1H-1,2,3-triazole

HRID 2074118Notes

Reaction equation

HRID 2074118 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][C:11]([C:13]2[N:14]=[N:15][N:16]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)=O)=[CH:4][CH:3]=1.[NH2:28][NH2:29].O>CCO.CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[NH:29][N:28]=[C:11]([C:13]3[N:14]=[N:15][N:16]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH:17]=3)[CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 670922894-(4-fluorophenyl)-1-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]butane-1,3-dione

Product 1

HCID 670923504-[5-(4-fluorobenzyl)-1H-pyrazol-3-yl]-1-(4-methoxybenzyl)-1H-1,2,3-triazoleYield 86%

Reagents, catalysts & solvents 1

HCID 18476134Acetic acid ethanolSolvent

Procedure

To a mixture of 4-(4-fluorophenyl)-1-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]butane-1,3-dione (0.6 g, 1.6 mmol) and anhydrous EtOH/AcOH (20 mL/5 mL) was added dropwise NH2NH2.H2O (1.0 mL, 9.6 mmol) at 0° C. and the mixture was stirred at RT overnight. The mixture was evaporated, the residue washed with anhydrous Et2O (4×5 mL) and the resulting precipitate was dried in oven to yield the title compound (0.5 g, 84.0%) as a yellow solid.

Workup

  1. customThe mixture was evaporated
  2. washthe residue washed with anhydrous Et2O (4×5 mL)
  3. customthe resulting precipitate was dried in oven

Sources & evidence

ORD record
ord-391289aa483a423abd399f4d8993f3ef
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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