Cyanogen Bromide → HCID 59424654, compound

HRID 500801Notes

Reaction equation

HRID 500801 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:8])=[CH:5][N:4]=[CH:3]1.N#C[Br:20].[Al]>C(#N)C>[Br:20][C:3]1[N:2]([CH3:1])[C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 5359268AluminumHCID 59424499HCID 59424499, compound

Product 1

HCID 59424654HCID 59424654, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 115 (550 mg, 2.31 mmol) in acetonitrile (5 mL) was added cyanogen bromide (489 mg, 4.6 mmol). The reaction flask was covered with aluminum foil and the mixture was allowed to stir at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography (eluents 100% EtOAc to 30% MeOH/EtOAc), to afford title compound 116 as a beige solid (230 mg (31%). MS (m/z) 317.1/319.1 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (eluents 100% EtOAc to 30% MeOH/EtOAc)

Sources & evidence

ORD record
ord-1b7930357d4a40069efbb123be843cdb
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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