Pyridine → HCID 136353005, compound

HRID 336859Notes

Reaction equation

HRID 336859 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4][N:3]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27].[OH-].[Na+]>O1CCCC1>[C:11]([C:8]1[CH:9]=[C:10]2[C:2]([NH:1][C:26](=[O:28])[CH3:27])=[N:3][NH:4][C:5]2=[N:6][C:7]=1[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)#[N:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 178509420HCID 178509420, compound

Product 1

HCID 136353005HCID 136353005, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 165 mg (0.66 mmol) of 3-amino-6-(4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile obtained following general procedure D1 and of 180 μL (2.16 mmol) of pyridine diluted in 1.6 ml of anhydrous tetrahydrofuran, are added dropwise at 0° C. 168 mg (2.16 mmol) of acetyl chloride. The solution is stirred under reflux for 4 h, then 655 μL (5M, 3.28 mmol) of sodium hydroxide solution are added, and the mixture is stirred for 1 h30 at 40° C. The tetrahydrofuran is concentrated and the solution is brought to acid pH (in the order of 3/4). The solid is filtered, washed with water, dried, and triturated in ethanol to yield 70 mg of N-(5-cyano-6-(4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-3-yl)acetamide in the form of a yellow solid.

Workup

  1. customobtained
  2. additionare added dropwise at 0° C
  3. temperatureunder reflux for 4 h
  4. stirringthe mixture is stirred for 1 h30 at 40° C
  5. concentrationThe tetrahydrofuran is concentrated
  6. filtrationThe solid is filtered
  7. washwashed with water
  8. customdried
  9. customtriturated in ethanol

Sources & evidence

ORD record
ord-aca4a3b9f7114bc7b9b3fdf4c2f7579f
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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