Hydrochloric Acid → HCID 178524461, compound

HRID 2264227Notes

Reaction equation

HRID 2264227 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[NH:33][C:15]3=[N:16][C:17]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[C:18]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][C:21]=4[F:26])[CH:19]=[C:14]3[N:13]=2)=[CH:7][CH:6]=1)C.Cl>C(O)C.[OH-].[Na+]>[F:26][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:20]=1[C:18]1[CH:19]=[C:14]2[N:13]=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:34])=[O:3])=[CH:6][CH:7]=3)[NH:33][C:15]2=[N:16][C:17]=1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178468996HCID 178468996, compound

Product 1

HCID 178524461HCID 178524461, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-[6-(3-fluoro-pyridin-4-yl)-5-pyridin-3-yl-3H-imidazo[4,5-b]pyridin-2-ylamino]-benzoic acid ethyl ester (0.120 g, 0.264 mmol) in ethanol (3.5 mL), 2N sodium hydroxide aqueous solution (0.53 mL) was added. The mixture was stirred at room temperature overnight and then neutralised with 2N hydrogen chloride aqueous solution. The solvent was evaporated and the crude mixture (0.18 g) was purified by reverse phase chromatography (water/acetonitrile) to give the title compound (0.02 g, 18% of yield).

Workup

  1. customThe solvent was evaporated
  2. customthe crude mixture (0.18 g) was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-cf85e54073264cbda77672e265ac6c23
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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