Sodium Hydroxide → HCID 86703409, compound

HRID 1909176Notes

Reaction equation

HRID 1909176 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:16]([O:18]CC)=O)[C:7]2[CH:12]=[N:11][N:10]([CH:13]([CH3:15])[CH3:14])[C:8]=2[N:9]=1.[NH2:21][CH2:22][C:23]1[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=1[CH3:29].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CCO.CS(C)=O>[Br:3][C:4]1[CH:5]=[C:6]([C:16]([NH:21][CH2:22][C:23]2[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=2[CH3:29])=[O:18])[C:7]2[CH:12]=[N:11][N:10]([CH:13]([CH3:14])[CH3:15])[C:8]=2[N:9]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 2724699PyBOPHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 86703408ethyl 6-bromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 86703409HCID 86703409, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Aqueous NaOH (0.964 g, 24.11 mmol) was added to a solution of ethyl 6-bromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (5 g, 16.07 mmol) in EtOH (50 mL) and stirred at 60° C. for 1 h. After completion of the reaction, ethanol was removed under reduced pressure and it was acidified using 10% citric acid solution. Extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The crude acid (3 g, 10.55 mmol) was then dissolved in DMSO (35 mL) and 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (3.2 g, 21.0 mmol) was added to it. The reaction mixture was stirred at room temperature for 15 min before PYBOP (8.23 g, 15.82 mmol) was added to it and stirring was continued overnight. After completion of the reaction, reaction mass was poured into ice to obtain solid, which was filtered and washed with acetonitrile followed by ether to provide the desired intermediate (3 g, 68%).

Workup

  1. customwas removed under reduced pressure and it
  2. extractionExtraction
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionwas added to it
  8. stirringstirring
  9. waitwas continued overnight
  10. customAfter completion of the reaction, reaction mass
  11. additionwas poured into ice
  12. customto obtain solid, which
  13. filtrationwas filtered
  14. washwashed with acetonitrile

Sources & evidence

ORD record
ord-5330f056fee04a83ada9be5c21274b40
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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