Hydrogen Bromide → HCID 118598739, compound

HRID 1050358Notes

Reaction equation

HRID 1050358 reaction equation
Br.[Br:2][C:3]1[C:8](=[O:9])[N:7]2[C:10]3([NH:37][C:38](=[O:39])[C:6]2=[C:5]([Cl:40])[CH:4]=1)[CH2:16][N:15](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:14][CH2:13][N:12](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:11]3>C(O)(=O)C.O1CCOCC1>[Br:2][C:3]1[C:8](=[O:9])[N:7]2[C:10]3([NH:37][C:38](=[O:39])[C:6]2=[C:5]([Cl:40])[CH:4]=1)[CH2:11][NH:12][CH2:13][CH2:14][NH:15][CH2:16]3

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 118598814HCID 118598814, compound

Product 1

HCID 118598739HCID 118598739, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of hydrogenbromide (1.43 g, 15.24 mmol) in acetic acid in 1,4-dioxane (30 mL), 6-bromo-8-chloro-1′,4′-ditosyl-2H-spiro[imidazo[1,5-a]pyridine-3,6′-[1,4]diazepane]-1,5-dione (1 g, 1.52 mmol) was added at room temperature. The vial was sealed and heated the reaction mass to 100° C. for 16 h. After completion, solvent was removed under reduced pressure and crude was triturated with dichloromethane to afford 6-bromo-8-chloro-2H-spiro[imidazo[1,5-a]pyridine-3,6′-[1,4]diazepane]-1,5-dione (4) as brown solid. Yield: 0.5 g, 94%; MS (ESI) m/z 362.28 [M+1]+.

Workup

  1. customThe vial was sealed
  2. customAfter completion, solvent was removed under reduced pressure and crude
  3. customwas triturated with dichloromethane

Sources & evidence

ORD record
ord-4a59d44f27f34bfeacf167c7ebe7951a
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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