Hydrochloric Acid → HCID 178524226, compound

HRID 2264202Notes

Reaction equation

HRID 2264202 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]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH: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]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH: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 178497563HCID 178497563, compound

Product 1

HCID 178524226HCID 178524226, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-3H-imidazo[4,5-b]pyridin-2-yl]benzoate (Example 10, 0.041 g, 0.097 mmol) in a mixture of THF/ethanol 1:1 (1.2 mL), 2N sodium hydroxide aqueous solution (0.1 mL) was added. The mixture was heated at 60° C. for 3 h and then neutralised with 2N hydrogen chloride aqueous solution. The solvent was evaporated and the crude mixture was purified by silica gel flash chromatography (78:10:10:2 dichloromethane/ethanol/ethyl acetate/acetic acid) to give the title compound (0.013 g, 31% of yield).

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe crude mixture was purified by silica gel flash chromatography (78:10:10:2 dichloromethane/ethanol/ethyl acetate/acetic acid)

Sources & evidence

ORD record
ord-dd2e4a9135d84188904e373e82485eb5
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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