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(R)-Benzyl (1-(4-((1H-pyrrolo[2,3-b]pyridin-4-yl)carbamoyl)phenyl)ethyl)carbamate → (R)-4-(1-Aminoethyl)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)benzamide dihydrochloride

HRID 619262
Notes
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Reaction equation

HRID 619262 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)[CH3:19])=[CH:14][CH:13]=3)=[C:4]2[CH:3]=[CH:2]1.[ClH:32].CO.[H][H]>[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].CO>[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]=[CH:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 12109146(R)-Benzyl (1-(4-((1H-pyrrolo[2,3-b]pyridin-4-yl)carbamoyl)phenyl)ethyl)carbamateHCID 21893726Hydrochloride methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 20601328(R)-4-(1-Aminoethyl)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)benzamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 178420936
HCID 178420936, compound
Catalyst
HCID 887MethanolSolvent

Procedure

10% Palladium hydroxide carbon (80 mg) was added to a mixture of (R)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-benzyloxycarbonylaminoethyl)benzamide (200 mg), 15% hydrochloric acid-methanol (1 ml) and methanol (6 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-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide dihydrochloride 3/2 hydrate having a melting point of 286° 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-d1377f8e7f974b5eb4b6a78a51f135d9
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05958944

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes