HCID 178418361, compound → HCID 178422281, compound

HRID 2115257Notes

Reaction equation

HRID 2115257 reaction equation
[CH3:1][C:2]1[C:28]([CH3:29])=[CH:27][C:5]2[NH:6][C:7]([C:9]3[NH:10][N:11]=[C:12]4[C:17]=3[CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][N:19]=3)[CH2:13]4)=[N:8][C:4]=2[CH:3]=1.[H][H]>C(O)C.[Pd].C([O-])([O-])=O.[Ca+2]>[CH3:1][C:2]1[C:28]([CH3:29])=[CH:27][C:5]2[NH:6][C:7]([C:9]3[NH:10][N:11]=[C:12]4[C:17]=3[CH2:16][CH2:15][N:14]([C:18]3[N:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[CH2:13]4)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178422282HCID 178422282, compound

Product 1

HCID 178422281HCID 178422281, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 702EthanolSolvent

Procedure

55 mg of Pd/CaCO3 10% are added to a solution of 545 mg of 3-(5,6-dimethyl-1H-benzimidazol-2-yl)-6-(5-nitropyridin-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine in 60 ml of ethanol. After stirring for 15 hours at 35° C. under 3 bar of hydrogen, the reaction medium is brought back to ambient temperature, filtered through celite and then concentrated under reduced pressure. 300 mg of 6-[3-(5,6-dimethyl-1H-benzimidazol-2-yl)-2,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl]-pyridin-3-ylamine are thus obtained in the form of a brown powder, the characteristics of which are as follows:

Workup

  1. customis brought back to ambient temperature
  2. filtrationfiltered through celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a91a50e1edb843919844e35fc5f1a5a6
Source dataset
uspto-grants-2008_10
Patent number
US07435820B2

Reaction notes

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