Cyanogen Bromide → HCID 59424654, compound

HRID 1261240Notes

Reaction equation

HRID 1261240 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-d5d29088300047b5ada0b00bcaa98ea4
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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