Cyanogen Bromide → HCID 67312396, compound

HRID 1890341Notes

Reaction equation

HRID 1890341 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([NH2:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:23]#[C:24]Br>CCO.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:24]([NH2:23])=[N:22][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 10476Cyanogen BromideHCID 67312740HCID 67312740, compound

Product 1

HCID 67312396HCID 67312396, compoundYield 13.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 6-(benzyloxy)-N2-phenylpyridine-2,3-diamine (3.106 g, 10.66 mmol), and cyanogen bromide (1.694 g, 15.99 mmol) in EtOH (50 mL) was stirred overnight at room temperature. The mixture was diluted with EtOAc and saturated NaHCO3. The layers were separated and the aqueous phase was back-extracted with EtOAc. The organics were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (446 mg). LCMS m/z=317.1 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was back-extracted with EtOAc
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7c57e05abe944a13a0f942e4dc3bf626
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

Loading…