Ethanol → HCID 68295072, compound

HRID 1909167Notes

Reaction equation

HRID 1909167 reaction equation
OCC1C=CC([C:9]2[C:17]3[C:16]([C:18]([O-:20])=O)=[CH:15][CH:14]=[N:13][C:12]=3[N:11]([CH:21]([CH3:23])[CH3:22])[N:10]=2)=CC=1.[OH-].[Na+].[NH2:26][CH2:27][C:28]1[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34].[C:37]([O-:40])(O)=O.[Na+].[CH3:42][CH2:43]O>CS(C)=O.CO.C(Cl)Cl>[CH3:34][C:33]1[CH:32]=[C:31]([CH3:35])[NH:30][C:29](=[O:36])[C:28]=1[CH2:27][NH:26][C:18]([C:16]1[C:17]2[CH:9]=[N:10][N:11]([CH:21]([CH3:22])[CH3:23])[C:12]=2[N:13]=[C:14]([C:43]2[CH:42]=[CH:17][C:16]([CH2:37][OH:40])=[CH:15][CH:14]=2)[CH:15]=1)=[O:20]

Participants

8

Reactant 5

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 86703406HCID 86703406, compound

Product 1

HCID 68295072HCID 68295072, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 6-(4-(hydroxymethyl)phenyl-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (0.81 g, 2.38 mmol) in EtOH (15 mL), aqueous NaOH (0.47 g, 11.94 mmol) was added and reaction mixture 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 5% MeOH/DCM. The combined organic layers were washed with water & dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford compound which was pure enough to use as such for next step. A solution of acid compound (0.61 g, 1.96 mmol) and 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (0.596 g, 3.92 mmol) in DMSO (5 mL) and was stirred at room temperature for 15 min. Then PYB OP (1.52 g, 2.94 mmol) was added to it and stirring was continued for 12 hr. After completion of the reaction, saturated NaHCO3 solution was added to it and extraction was carried out using 20% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to afford the desired compound as white solid (0.71 g, 81.4%).

Workup

  1. customreaction mixture
  2. customwas removed under reduced pressure and it
  3. extractionExtraction
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford compound which
  9. additionThen PYB OP (1.52 g, 2.94 mmol) was added to it
  10. stirringstirring
  11. waitwas continued for 12 hr
  12. additionwas added to it and extraction
  13. washThe combined organic layers were washed with water
  14. dry with materialdried over anhydrous Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure
  17. customto afford crude material which
  18. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1605c9ff7bc340fa95ebdd04561a3cca
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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