Acetic Acid Mixture with Hydrobromic Acid → HCID 86754547, compound

HRID 619277Notes

Reaction equation

HRID 619277 reaction equation
[BrH:1].C(O)(=O)C.[NH:6]1[C:10]2=[N:11][CH:12]=[CH:13][C:14]([NH:15][C:16](=[O:39])[C:17]3[CH:22]=[CH:21][C:20]([C@H:23]([NH:25]C(OCC4C=CC=CC=4)=O)[CH3:24])=[C:19]([N:36]=[N+:37]=[N-:38])[CH:18]=3)=[C:9]2[CH:8]=[CH:7]1>>[BrH:1].[BrH:1].[NH:6]1[C:10]2=[N:11][CH:12]=[CH:13][C:14]([NH:15][C:16](=[O:39])[C:17]3[CH:22]=[CH:21][C:20]([C@H:23]([NH2:25])[CH3:24])=[C:19]([N:36]=[N+:37]=[N-:38])[CH:18]=3)=[C:9]2[CH:8]=[CH:7]1

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86754548HCID 86754548, compound

Product 1

HCID 86754547HCID 86754547, compound

Procedure

A 25% hydrogen bromide-acetic acid solution (4 ml) was added to (R)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-3-azido-4-(1-benzyloxycarbonylaminoethyl)benzamide (400 mg), and the mixture was stirred at room temperature for 1.5 hours. After the reaction, the solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from ethanol-ethyl acetate to give 285 mg of (R)-(-)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-aminoethyl)-3-azidobenzamide dihydrobromide 1/2 hydrate having a melting point of 216-219° C. (dec.) as white crystals.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained crystals were recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-c075e2e2c8af48fd83e9343efd84715d
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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