Cyanogen Bromide → [5-(5-Amino-[1,3,4]oxadiazol-2-yl)-7-fluoro-3-methyl-3h-imidazo[4,5-b]pyridin-6-yl]-(4-bromo-2-fluorophenyl)-amine

HRID 2102402Notes

Reaction equation

HRID 2102402 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([F:23])=[C:11]3[N:21]=[CH:20][N:19]([CH3:22])[C:12]3=[N:13][C:14]=2[C:15]([NH:17][NH2:18])=[O:16])=[C:4]([F:24])[CH:3]=1.Br[C:26]#[N:27].C([O-])(O)=O.[Na+]>O1CCOCC1.O>[NH2:27][C:26]1[O:16][C:15]([C:14]2[N:13]=[C:12]3[N:19]([CH3:22])[CH:20]=[N:21][C:11]3=[C:10]([F:23])[C:9]=2[NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:24])=[N:17][N:18]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 690025666-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid hydrazide

Product 1

HCID 11384665[5-(5-Amino-[1,3,4]oxadiazol-2-yl)-7-fluoro-3-methyl-3h-imidazo[4,5-b]pyridin-6-yl]-(4-bromo-2-fluorophenyl)-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3 -methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid hydrazide (1.00 equivalent) in 1,4-dioxane at room temperature is added BrCN (2.0 equivalents) followed by a solution of NaHCO3 (1.0 equivalents) 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 in vacuo to give the crude material that is purified by trituration or flash column chromatography to afford [5-(5-amino-[1,3,4]oxadiazol-2-yl)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl]-(4-bromo-2-fluorophenyl)-amine.

Workup

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

Sources & evidence

ORD record
ord-b0b05b2ffaae4479a00c7c1fee6486eb
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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