Water → 4-(1,3-benzodioxol-5-yl)-1-benzyl-3-methoxy-1H-pyrazol-5-amine

HRID 1062813Notes

Reaction equation

HRID 1062813 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].CI.[NH2:9][C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]=[C:12]([OH:22])[C:11]=1[C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1.O>CN(C)C=O>[O:27]1[C:26]2[CH:30]=[CH:31][C:23]([C:11]3[C:12]([O:22][CH3:1])=[N:13][N:14]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:10]=3[NH2:9])=[CH:24][C:25]=2[O:29][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178507199HCID 178507199, compound

Product 1

HCID 222819794-(1,3-benzodioxol-5-yl)-1-benzyl-3-methoxy-1H-pyrazol-5-amineYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (1.05 g) and methyl iodide (0.46 g) were sequentially added at room temperature under an atmosphere of nitrogen to a solution of 5-amino-4-(1,3-benzodioxol-5-yl)-1-benzyl-1H-pyrazol-3-ol (1.0 g) (Preparation 59) in anhydrous dimethylformamide (10 ml). After 10 h, the reaction mixture was diluted water (100 ml) and the mixture was extracted with ether (3×100 ml). The organic fractions were washed with brine (100 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The oily residue was purified by column chromatography (silica, 50 g) eluted with hexane:ethyl acetate (1:1) yielding the title compound as a white solid (260 mg).

Workup

  1. extractionthe mixture was extracted with ether (3×100 ml)
  2. washThe organic fractions were washed with brine (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe oily residue was purified by column chromatography (silica, 50 g)
  6. washeluted with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-0b825fbbd0a3497487770914e5151a8e
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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