HCID 12109149, compound → HCID 22120548, compound

HRID 619266Notes

Reaction equation

HRID 619266 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11](=[O:30])[C:12]3[CH:17]=[CH:16][C:15]([CH2:18][NH:19]C(OCC4C=CC=CC=4)=O)=[CH:14][CH:13]=3)=[C:4]2[CH:3]=[N:2]1.[ClH:31].CO.[H][H]>[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].CO>[ClH:31].[ClH:31].[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11](=[O:30])[C:12]3[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=3)=[C:4]2[CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 12109149HCID 12109149, compoundHCID 21893726Hydrochloride methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 22120548HCID 22120548, compound

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium hydroxide carbon (250 mg) was added to a mixture of N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-benzyloxycarbonylaminomethylbenzamide (540 mg), 15% hydrochloric acid-methanol (3 ml) and methanol (10 ml), and the mixture was stirred in a stream of hydrogen at 40° C. for 2 hours. After the reaction, the catalyst was removed by filtration, and the mixture was concentrated under reduced pressure. The obtained crystals were recrystallized from ethanol-ethyl acetate to give 330 mg of N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-aminomethylbenzamide dihydrochloride.

Workup

  1. customAfter the reaction
  2. customthe catalyst was removed by filtration
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe obtained crystals were recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-809e1dd9b9014bb4b50082f1756074db
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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