Water → HCID 178499647, compound

HRID 589408Notes

Reaction equation

HRID 589408 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[N:2]1.S(=O)(=O)(O)O.O.[C:20](=O)([O-])[O-].[K+].[K+]>CO>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([O:13][CH3:20])=[O:12])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 178525255HCID 178525255, compound

Product 1

HCID 178499647HCID 178499647, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

2-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetic acid (317 mg a crude) was dissolved in 15 mL methanol, and concentrated sulfuric acid 0.5 mL was added dropwise. It was heated to 70° C. and reacted for 12 hours. The reaction was monitored to be complete by LC-MS. 50 mL water was added, and the pH was adjusted to be weak basic with potassium carbonate. Methanol was rotate evaporated. It was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and rotate evaporated to dryness to obtain a light yellow solid 250 mg, at a yield over two steps of 73.6%.

Workup

  1. customreacted for 12 hours
  2. customevaporated
  3. extractionIt was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate, and rotate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ba5652ea391345568ad81be9e674c843
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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