Water → HCID 86610065, compound

HRID 1911741Notes

Reaction equation

HRID 1911741 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:13]=[C:12]2[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]2=[CH:10][C:9]=1[CH:19]=[O:20].[CH2:21]([NH:23][CH2:24][C@@H:25]1[CH2:29][CH2:28][CH2:27][O:26]1)[CH3:22].O>CN(C)C=O.C(OCC)(=O)C>[CH2:21]([N:23]([CH2:24][C@@H:25]1[CH2:29][CH2:28][CH2:27][O:26]1)[C:8]1[N:13]=[C:12]2[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]2=[CH:10][C:9]=1[CH:19]=[O:20])[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 162286606-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeHCID 40152800HCID 40152800, compound

Product 1

HCID 86610065HCID 86610065, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.42 g, 3 mmol) was added to a solution of 6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (0.46 g, 2.2 mmol) and (S)-(+)-ethyl-(tetrahydro-furan-2-ylmethyl)-amine (4.8 mmol) in anhydrous dimethyl formamide (6 mL) under nitrogen. After stirring for 0.5 h at RT, the reaction mixture was heated for 20 h at 80-95° C. Thereafter, the reaction was cooled to RT, water (30 mL) and ethyl acetate (30 mL) were added, and the organic layer was separated from the aqueous mixture. The organic extract was washed with brine, dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by chromatography using silica gel (200-400 mesh) to afford the title compound as a pale yellow liquid (0.35 g, yield: 53%).

Workup

  1. temperaturethe reaction mixture was heated for 20 h at 80-95° C
  2. temperatureThereafter, the reaction was cooled to RT
  3. customthe organic layer was separated from the aqueous mixture
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-377d4a9f308d49e08cb4f3f0219a56e6
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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