Hydrochloric Acid → HCID 178524815, compound

HRID 2264218Notes

Reaction equation

HRID 2264218 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[C:10]2[N:22]=[C:21]([N:23]3[CH:27]=[C:26]([C:28]([O:30]CC)=[O:29])[CH:25]=[N:24]3)[NH:20][C:11]2=[N:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[OH-].[Na+].Cl>C1COCC1.C(O)C>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[C:10]2[N:22]=[C:21]([N:23]3[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[N:24]3)[NH:20][C:11]2=[N:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178469988HCID 178469988, compound

Product 1

HCID 178524815HCID 178524815, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 1-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-3H-imidazo[4,5-b]pyridin-2-yl]-1H-pyrazole-4-carboxylate (0.022 g, 0.05 mmol) in a mixture of THF/ethanol 1:1 (1 mL), 2N sodium hydroxide aqueous solution (0.05 mL) was added. The mixture was heated at 60° C. for 2 hours and then neutralised with 2N hydrogen chloride aqueous solution. The solvent was evaporated and the crude mixture was purified by solid phase extraction, SCX, it was washed with water and eluted with methanol/ammonia (9:1) to give the title compound (0.007 g, 29% of yield).

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe crude mixture was purified by solid phase extraction, SCX, it
  4. washwas washed with water
  5. washeluted with methanol/ammonia (9:1)

Sources & evidence

ORD record
ord-27d4ce62cd154abb91f19ae819ebf763
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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