Ethanol → HCID 16791219, compound

HRID 1522427Notes

Reaction equation

HRID 1522427 reaction equation
[CH3:1][C:2]1[CH:3]=C(C#N)[C:5]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>O>[CH3:1][C:2]1[CH:3]=[C:23]([C:22]([OH:20])=[O:24])[C:5]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67124107HCID 67124107, compound

Product 1

HCID 16791219HCID 16791219, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Methyl-1-(phenylmethyl)-1H-pyrazolo[3,4-b]pyridine-4-carbonitrile (1 g), sodium hydroxide (0.805 g, 20.14 mmol), ethanol (25 mL) and water (10 mL) were heated at reflux for 2 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The crude product was suspended in water (50 mL) and acidified by dropwise addition of 6N HCl. The solid product was filtered off and dissolved in 100 ml of EtOAc. The solution dried over MgSO4, filtered, and concentrated in vacuo. The final product was obtained as 0.730 g. LCMS E-S (M+H)=267.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.71 (s, 3 H), 5.70 (s, 2 H), 7.15-7.37 (m, 5 H), 7.63 (s, 1 H), 8.33 (s, 1 H), 13.86 (s, 1 H).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solvent was removed under reduced pressure
  3. additionacidified by dropwise addition of 6N HCl
  4. filtrationThe solid product was filtered off
  5. dissolutiondissolved in 100 ml of EtOAc
  6. dry with materialThe solution dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cab95b91b974a22b0afc5b78defe157
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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