Acetic Acid Mixture with Hydrobromic Acid → HCID 86754547, compound

HRID 1274194Notes

Reaction equation

HRID 1274194 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-8e1d4cd94de44d45adf743ba08450c7b
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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