Cyanogen Bromide → HCID 59424209, compound

HRID 500575Notes

Reaction equation

HRID 500575 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([F:25])[C:8]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=3[F:24])=[C:9]([C:12]([NH:14][NH2:15])=[O:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.Br[C:27]#[N:28].C([O-])(O)=O.[Na+]>O1CCOCC1.O>[NH2:28][C:27]1[O:13][C:12]([C:9]2[CH:10]=[C:11]3[C:6](=[C:7]([F:25])[C:8]=2[NH:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[F:24])[N:5]=[N:4][CH:3]=[C:2]3[NH2:1])=[N:14][N:15]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 68637515HCID 68637515, compound

Product 1

HCID 59424209HCID 59424209, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 4-amino-7-(4-bromo-2-fluorophenylamino)-8-fluorocinnoline-6-carboxylic acid hydrazide (1.00 equiv.) in 1,4-dioxane at room temperature is added BrCN (2.00 equiv.) followed by a solution of NaHCO3 (1.00 equiv.) in H2O. After stirring for 3 hours at room temperature, the reaction mixture is diluted with water and extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that is purified by trituration or flash column chromatography to afford 6-(5-amino-[1,3,4]oxadiazol-2-yl)-N7-(4-bromo-2-fluoro-phenyl)-8-fluorocinnoline-4,7-diamine.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude material that
  7. customis purified by trituration or flash column chromatography

Sources & evidence

ORD record
ord-7a5bb89ea27c4ebc9d5d42e260faa434
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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