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

HRID 510042Notes

Reaction equation

HRID 510042 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([N+:18]([O-])=O)=[CH:13][CH:12]=3)[N:9]=[C:8]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:5]2=[N:6][CH:7]=1.[H][H]>N1C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[CH:13][CH:12]=3)[N:9]=[C:8]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 666140776-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-3-nitropyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 666141476-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

300 mg (0.785 mmol) of the compound from example 39A were initially charged in pyridine (35 ml), then 119 mg of palladium (10% on charcoal) were added and the mixture was hydrogenated at standard hydrogen pressure overnight. The reaction mixture was filtered through kieselguhr and washed through with ethanol, and the filtrate was concentrated. This gave 219 mg (92% purity, 73% of theory) of the title compound in solid form.

Workup

  1. filtrationThe reaction mixture was filtered through kieselguhr
  2. washwashed through with ethanol
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9b4345d3e8524f7ca1455d679b6ec140
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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