Hydrochloric Acid → HCID 28824750, compound

HRID 130892Notes

Reaction equation

HRID 130892 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][CH:11]=2)=[N:7][CH:8]=1)#[N:2].Cl>C1COCC1.CCO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][CH:11]=2)=[N:7][CH:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 28825081HCID 28825081, compound

Product 1

HCID 28824750HCID 28824750, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine 4-(5-cyano-pyridin-2-yloxy)-benzamide (202 mg, 0.844 mmol), 5% Pd/C (80 mg) and conc. HCl (0.423 mL) in THF (4 mL) and EtOH (4 mL). Run the reaction under hydrogen atmosphere (1 atm) at rt overnight. Add NaOH (5 N, 2 mL) and filter the reaction mixture through Celite®. Concentrate the filtrate. Wash the residue with H2O (5 mL) and extract with CH2Cl2 (3×5 mL). Combine the organic layers and purify through an SCX column eluting with 2M ammonia in methanol. Concentrate the fractions to give the title compound (74 mg, 36%).

Workup

  1. customthe reaction under hydrogen atmosphere (1 atm) at rt overnight
  2. filtrationAdd NaOH (5 N, 2 mL) and filter the reaction mixture through Celite®
  3. concentrationConcentrate the filtrate
  4. washWash the residue with H2O (5 mL)
  5. extractionextract with CH2Cl2 (3×5 mL)
  6. customCombine the organic layers and purify through an SCX column
  7. washeluting with 2M ammonia in methanol
  8. concentrationConcentrate the fractions

Sources & evidence

ORD record
ord-5238f1994dd2433f914f1389d4121b43
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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