6-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-3-nitropyridin-2-amine → 6-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyridine-2,3-diamine

HRID 510044Notes

Reaction equation

HRID 510044 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([N+:21]([O-])=O)=[CH:16][CH:15]=2)=[N:6]1>N1C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][CH:15]=2)=[N:6]1

Participants

4

Reactant 1

HCID 666135626-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-3-nitropyridin-2-amine

Product 1

HCID 666140516-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

1.22 g (approx. 3.34 mmol, purity approx. 60%) of the compound from example 42A were initially charged in pyridine (149 ml) and then 505 mg (0.47 mmol) of palladium (10% on charcoal) were added. The mixture was hydrogenated under standard hydrogen pressure at RT overnight. The reaction mixture was then filtered through kieselguhr and the filtercake was washed with methanol. The filtrate was concentrated, methanol was added and the solids were filtered off. The filtrate was concentrated by rotary evaporation, the residue was chromatographed on silica gel (eluent: 5:1, 3:1 cyclohexane/ethyl acetate) and the product fractions were concentrated. This gave 491 mg (44% of theory) of the title compound.

Workup

  1. customat RT
  2. customovernight
  3. filtrationThe reaction mixture was then filtered through kieselguhr
  4. washthe filtercake was washed with methanol
  5. concentrationThe filtrate was concentrated
  6. additionmethanol was added
  7. filtrationthe solids were filtered off
  8. concentrationThe filtrate was concentrated by rotary evaporation
  9. customthe residue was chromatographed on silica gel (eluent: 5:1, 3:1 cyclohexane/ethyl acetate)
  10. concentrationthe product fractions were concentrated

Sources & evidence

ORD record
ord-a457f6f5f7ec4b29808705dbe999c99e
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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