Ethyl chloroacetate → HCID 15158100, compound

HRID 1084851Notes

Reaction equation

HRID 1084851 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][N:13]=2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C)C=O>[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 178483742HCID 178483742, compound

Product 1

HCID 15158100HCID 15158100, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 6 g of 3-[4-(2-dimethylaminoethylamino)phenyl]-1H-pyrazolo[3,4-b]pyridine, 5 g of potassium carbonate and 60 ml of dimethylformamide was added dropwise 4.6 g of ethyl chloroacetate. The mixture was stirred at 50° C. for 4 hours. After the solvent was distilled off, the residue was dissolved in ethyl acetate and washed with water. After ethyl acetate was distilled off, the residue was purified by column chromatography to give ethyl 3-[4-(2-dimethylaminoethylamino)phenyl]-1H-pyrazolo[3,4-b]pyridin-1-ylacetate in an oily form.

Workup

  1. distillationAfter the solvent was distilled off
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. distillationAfter ethyl acetate was distilled off
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-41d612911079476ba1ba67bb8d693081
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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