HCID 12109147, compound → HCID 18392473, compound

HRID 619264Notes

Reaction equation

HRID 619264 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11](=[O:31])[C:12]3[CH:17]=[CH:16][C:15]([C@H:18]([NH:20]C(OCC4C=CC=CC=4)=[O:22])[CH3:19])=[CH:14][CH:13]=3)=[C:4]2[CH:3]=[N:2]1.[ClH:32].CO.[H][H]>[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].CO>[OH2:22].[ClH:32].[ClH:32].[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11](=[O:31])[C:12]3[CH:17]=[CH:16][C:15]([C@H:18]([NH2:20])[CH3:19])=[CH:14][CH:13]=3)=[C:4]2[CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 12109147HCID 12109147, compoundHCID 21893726Hydrochloride methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 18392473HCID 18392473, compound

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium hydroxide carbon (100 mg) was added to a mixture of (R)-N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-(1-benzyloxycarbonylaminoethyl)benzamide (300 mg), 15% hydrochloric acid-methanol (3 ml) and methanol (14 ml), and the mixture was stirred in a stream of hydrogen at 40° C. for 1 hour. After the reaction, the catalyst was removed by filtration, and the mixture was concentrated under reduced pressure. The obtained crystals were recrystallized from methanol-ether to give 120 mg of (R)-(+)-N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide dihydrochloride monohydrate having a melting point of 259° C. (dec.).

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 methanol-ether

Sources & evidence

ORD record
ord-bb6ecec3ac9546aca9951915d50495cf
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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