Sodium Hydroxide → HCID 68295072, compound

HRID 1501533Notes

Reaction equation

HRID 1501533 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].C1CN([P+](ON2N=N[C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][C:55]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:70]([O-])(O)=[O:71].[Na+]>CCO.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:59]2[CH:60]=[CH:55][C:56]([CH2:70][OH:71])=[CH:57][CH:58]=2)[CH:15]=1)=[O:20]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 86703406HCID 86703406, compound

Product 1

HCID 68295072HCID 68295072, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent2×HCID 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 PYBOP (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. stirringstirring
  10. waitwas continued for 12 hr
  11. additionwas added to it and extraction
  12. washThe combined organic layers were washed with water
  13. dry with materialdried over anhydrous Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure
  16. customto afford crude material which
  17. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a0a378d37af24696a10729cc7d25c709
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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