Water → HCID 23400310, compound

HRID 397278Notes

Reaction equation

HRID 397278 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([OH:8])[C:3]=1[C:9]1[CH:17]=[CH:16][C:12]2[O:13][CH2:14][O:15][C:11]=2[CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][CH2:26][O:27][C:28](=[O:30])[CH3:29].O>CN(C)C=O>[C:28]([O:27][CH2:26][CH2:25][O:8][C:4]1[C:3]([C:9]2[CH:17]=[CH:16][C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=2)=[C:2]([NH2:1])[N:6]([CH3:7])[N:5]=1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178481945HCID 178481945, compound

Product 1

HCID 23400310HCID 23400310, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-amino-4-(1,3-benzodioxol-5-yl)-1-methyl-1H-pyrazol-3-ol (Preparation 16) (11.39 g) was dissolved in dimethylformamide (40 mm), caesium carbonate (15.9 g) was added followed by 2-bromoethylacetate (8.16 g). The mixture was stirred at room temperature for 16 hours. The mixture was treated with water (750 ml) and extracted with ethyl acetate (2×250 ml). The organic fractions were combined washed with water (3×350 ml), brine (250 ml), dried over magnesium sulfate, filtered and evaporated. The crude product was purified on. silica (300 g) eluting with ethyl acetate:hexane (3:1) to yield the title compound as a white solid (5.57 g).

Workup

  1. extractionextracted with ethyl acetate (2×250 ml)
  2. washThe organic fractions were combined washed with water (3×350 ml), brine (250 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified on
  7. washsilica (300 g) eluting with ethyl acetate:hexane (3:1)

Sources & evidence

ORD record
ord-9a18c8c753594ef6ac9d3248bad502fd
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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