Hydrochloric Acid → HCID 67074198, compound

HRID 336855Notes

Reaction equation

HRID 336855 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]3[NH:15][N:16]=[CH:17][C:12]3=[C:11]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[C:10]=2[C:23]#[N:24])=[CH:5][CH:4]=1)#N.[OH-:25].[K+].C[OH:28].Cl>O1CCOCC1.O>[C:23]([C:10]1[C:11]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[C:12]2[CH:17]=[N:16][NH:15][C:13]2=[N:14][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([C:1]([OH:28])=[O:25])=[CH:8][CH:7]=1)#[N:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 51348382HCID 51348382, compound

Product 1

HCID 67074198HCID 67074198, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.10 g (0.32 mmol) of 6-(4-cyanophenyl)-4-(furan-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and 0.22 g (4.0 mmol) of potassium hydroxide in a mixture of 2 ml of dioxane, 2 ml of MeOH, and 0.75 ml of water is refluxed for 24 h. Next, the mixture is cooled, acidified with 1N HCl, then extracted with ethyl acetate and dichloromethane. The organic phase is dried over sodium sulfate, filtered and concentrated to give 0.018 g (17%) of 4-(5-cyano-4-(furan-2-yl)-1H-pyrazolo[3,4-b]pyridine-6-yl)benzoic acid in the form of brown crystals.

Workup

  1. temperatureis refluxed for 24 h
  2. temperatureNext, the mixture is cooled
  3. extractionextracted with ethyl acetate and dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e8e84b209074ddbbb49c5349ffc8fc5
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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