Water → 6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

HRID 1911731Notes

Reaction equation

HRID 1911731 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]2=[CH:4][C:3]=1[CH:13]=[O:14].C(=O)([O-])[O-].[K+].[K+].[CH:21]1([CH2:26][NH:27][CH2:28][CH3:29])[CH2:25][CH2:24][CH2:23][CH2:22]1.O>CN(C=O)C>[CH:21]1([CH2:26][N:27]([CH2:28][CH3:29])[C:2]2[N:7]=[C:6]3[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]3=[CH:4][C:3]=2[CH:13]=[O:14])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 162286606-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeHCID 43163716N-(cyclopentylmethyl)-N-ethylamine

Product 1

HCID 574868046-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (5 g, 0.023 mol) and potassium carbonate (9.9 g, 0.0717 mol) in DMF (75 mL) was stirred for 20 min at RT. Cyclopentylmethyl ethyl amine (4.25 g, 33.0 mmol) was then added and the reaction was refluxed for 8 h. After cooling the reaction to RT, water (500 mL) was added to the reaction mixture and extracted with ethyl acetate (3×400 mL) and the combined organic layers were dried and concentrated. The residue was purified by silica gel (100-200 mesh) column chromatography. Elution with 10% ethyl acetate in hexanes gave the pure product as a colorless, gummy mass (yield: 76%).

Workup

  1. temperaturethe reaction was refluxed for 8 h
  2. temperatureAfter cooling
  3. customthe reaction to RT
  4. extractionextracted with ethyl acetate (3×400 mL)
  5. customthe combined organic layers were dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel (100-200 mesh) column chromatography
  8. washElution with 10% ethyl acetate in hexanes
  9. customgave the pure product as a colorless, gummy mass (yield: 76%)

Sources & evidence

ORD record
ord-1cff4b94aa0444298cd3d5ab49dec5fb
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

Loading…