[2-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-hydrazine → 3-(3,5-Diethyl-pyrazol-1-yl)-2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridine

HRID 2180002Notes

Reaction equation

HRID 2180002 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][NH2:10])=[CH:7][C:6]([CH3:11])=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[O:23][CH3:24])[N:4]=1>CCO>[CH2:7]([C:6]1[CH:5]=[C:12]([CH2:13][CH3:14])[N:9]([C:8]2[C:3]([O:2][CH3:1])=[N:4][C:5]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:21])([F:22])[F:20])=[CH:14][C:13]=3[O:23][CH3:24])=[C:6]([CH3:11])[CH:7]=2)[N:10]=1)[CH3:8]

Participants

3

Reactant 1

HCID 22490050[2-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-hydrazine

Product 1

HCID 101814093-(3,5-Diethyl-pyrazol-1-yl)-2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of 3-(3,5-Diethyl-pyrazol-1-yl)-2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridine 3,5-heptane dione (0.32 ml, 2.33 mmol) is added to a solution of [2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-hydrazine (0.8 g, 2.33 mmol) in EtOH (15 ml) at room temperature. The mixture is refluxed for 15 hours. The solvent is removed under reduced pressure and the residue is purified by flash column chromatography to obtain 3-(3,5-Diethyl-pyrazol-1-yl)-2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridine (Compound 4). Rf(hexane/EtOAc=9:1)=0.18, MS m/z 436.4 (M+H).

Workup

  1. temperatureThe mixture is refluxed for 15 hours
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-d08e34b4cbcf45219756d57e2faba052
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Reaction notes

Loading…