HCID 67088872, compound → HCID 178508018, compound

HRID 1943897Notes

Reaction equation

HRID 1943897 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:12]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][N:10](COCC[Si](C)(C)C)[C:7]2=[N:8][CH:9]=1)([O-])=O>C(OCC)(=O)C>[C:14]1([NH:13][C:12]2[C:6]3[C:7](=[N:8][CH:9]=[C:4]([NH2:1])[CH:5]=3)[NH:10][N:11]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 67088872HCID 67088872, compound

Product 1

HCID 178508018HCID 178508018, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

SnCl2 dihydrate (0.243 g, 1.28 mmol) was added to a suspension of 5-nitro-N-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-amine (0.099 g, 0.257 mmol) in ethyl acetate (25 mL), and the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and quenched with saturated aqueous NaHCO3 (25 mL). The resulting suspension was filtered through a pad of celite, and the filter cake was washed with ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (1:1), hexanes/ethyl acetate (1:2) to give N3-phenyl-1H-pyrazolo[3,4-b]pyridine-3,5-diamine (0.012 g, 21% over 3 steps) as solids.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customquenched with saturated aqueous NaHCO3 (25 mL)
  4. filtrationThe resulting suspension was filtered through a pad of celite
  5. washthe filter cake was washed with ethyl acetate (100 mL)
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography
  11. washeluting with hexanes/ethyl acetate (1:1), hexanes/ethyl acetate (1:2)

Sources & evidence

ORD record
ord-921a86acf05e42349d57b74a2a024465
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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