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

HRID 641160Notes

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>[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

Participants

Conditions

Temperature: 40 °C

Procedure

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) was added 10% palladium hydroxide carbon (80 mg), and the mixture was stirred under a hydrogen stream at 40° C. for 1 hr. After the reaction, the catalyst was filtered off and the residue was concentrated under reduced pressure. The obtained crystals were recrystallized from methanol-ether to give (R)-(+)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)benzamide dihydrochloride 3/2 hydrate (120 mg), melting point: 286° C. (decomposition).

Workup

customAfter the reaction
filtrationthe catalyst was filtered off
concentrationthe residue was concentrated under reduced pressure
customThe obtained crystals were recrystallized from methanol-ether

Sources & evidence

ORD record: ord-c96997cf57224ef6aa35eeafc756a0d6
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696194B2

Reaction notes

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