1-Ethyl-1H-pyrazol-5-amine → 1h-Pyrazolo[3,4-b]pyridine-5-carboxylic acid,4-(3-chlorophenyl)-1-ethyl-4,7-dihydro-6-methyl-,ethyl ester

HRID 2373207Notes

Reaction equation

HRID 2373207 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][CH:3]=1.[C:9]([C:12](=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=O)[CH3:10]>>[Cl:25][C:21]1[CH:20]=[C:19]([CH:18]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH3:10])[NH:1][C:2]3[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][C:3]2=3)[CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 3373101-Ethyl-1H-pyrazol-5-amineHCID 367058Ethyl 2-acetyl-3-(3-chlorophenyl)acrylate

Product 1

HCID 1362379411h-Pyrazolo[3,4-b]pyridine-5-carboxylic acid,4-(3-chlorophenyl)-1-ethyl-4,7-dihydro-6-methyl-,ethyl esterYield 34.9%

Conditions

Temperature
130 °C

Procedure

A mixture of 5-amino-1-ethylpyrazole (250 mg) and ethyl 2-acetyl-3-(3-chlorophenyl)acrylate (568 mg) was heated at 130° C. for 3 hours. After cooling, the residue was evaporated. The residue was diluted with CHCl3 and washed with saturated NaHCO3, water, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:7)-to give ethyl 4-(3-chlorophenyl)-1-ethyl-6-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (271 mg) as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. customthe residue was evaporated
  3. additionThe residue was diluted with CHCl3
  4. washwashed with saturated NaHCO3, water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:7)-to

Sources & evidence

ORD record
ord-339903f7dd4c445f93c9a8dc33ef0771
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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