Hydrochloric Acid → HCID 11487540, compound

HRID 2102400Notes

Reaction equation

HRID 2102400 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:15]=[C:14]2[N:16]([CH3:19])[CH:17]=[N:18][C:13]2=[C:12]([F:20])[C:11]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=1[F:29])=[O:9])=C.Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCO.CCOC(C)=O>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:15]=[C:14]2[N:16]([CH3:19])[CH:17]=[N:18][C:13]2=[C:12]([F:20])[C:11]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=1[F:29])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 865996086-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (2-vinyloxyethoxy)-amide

Product 1

HCID 11487540HCID 11487540, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3 -methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (2-vinyloxyethoxy)-amide (1.00 equivalent) in THF-EtOH is added 1 N aqueous HCl (2.0 equivalents) at room temperature. After stirring for 1 hour at room temperature, the reaction mixture is neutralized with saturated aqueous NaHCO3 and diluted 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 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (2-hydroxyethoxy)-amide.

Workup

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

Sources & evidence

ORD record
ord-bbcb7310f5114b91aa5ad1e0987c8495
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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