HCID 178520053, compound → HCID 178508017, compound

HRID 1943926Notes

Reaction equation

HRID 1943926 reaction equation
[CH:1]1([C:4]([C:6]2[C:14]3[C:9](=[N:10][CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=3)[NH:8][N:7]=2)=[O:5])[CH2:3][CH2:2]1>CCOC(C)=O.C(=O)(O)[O-]>[NH2:15][C:12]1[CH:13]=[C:14]2[C:6]([C:4]([CH:1]3[CH2:2][CH2:3]3)=[O:5])=[N:7][NH:8][C:9]2=[N:10][CH:11]=1

Participants

4

Reactant 1

HCID 178520053HCID 178520053, compound

Product 1

HCID 178508017HCID 178508017, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

SnCl2 dihydrate (0.24 g, 1.1 mmol) was added to cyclopropyl(5-nitro-1H-pyrazolo[3,4-b]pyridin-3-yl)methanone (0.050 g, 0.22 mmol) in EtOAc (1 mL). The reaction mixture was heated to reflux for 6 hours. The mixture was then cooled, diluted with EtOAc (5 mL), aqueous bicarbonate (5 mL) and filtered through celite. The organic layers were extracted with EtOAc (3×5 mL), dried over sodium sulfate, and concentrated to provide (5-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)(cyclopropyl)methanone (0.035 g, 0.17 mmol, 80% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered through celite
  5. extractionThe organic layers were extracted with EtOAc (3×5 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1c7ddb0e04b449c3a0d452f1e7559ff6
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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