Hydrochloric Acid → HCID 68527515, compound

HRID 884131Notes

Reaction equation

HRID 884131 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)=[CH:17][N:16]=2)=[CH:10][CH:9]=1)C.C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41].[OH-].[Na+].Cl>ClCCl.O>[C:40]([N:6]([CH2:5][C:4]([OH:3])=[O:32])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)=[CH:17][N:16]=2)=[CH:12][CH:13]=1)(=[O:42])[CH3:41]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 86671244HCID 86671244, compound

Product 1

HCID 68527515HCID 68527515, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl{4-[5-(3,4-dichloro-benzoylamino)pyridin-2-yloxy]benzylamino}acetate (0.811 g, 1.59 mmol) in dichloromethane (5 mL) were added triethylamine (0.332 mL, 2.39 mmol) and acetyl chloride (0.136 mL, 1.91 mmol) at room temperature. The resulting solution was stirred for 1 hour at the same temperature. To the reaction solution was added water, and extracted with dichloromethane. The dichloromethane layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated, to thereby yield 0.785 g of residue. This residue was dissolved in ethanol (5 mL). To the resulting solution was added 5 M aqueous sodium hydroxide (0.350 mL, 1.75 mmol) at room temperature and stirred at the same temperature for 14 hours. To the resulting reaction solution were added 5 M hydrochloric acid (0.400 mL) and water, and extracted with dichloromethane. The dichloromethane layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated, to thereby yield 0.776 g of the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. dissolutionThis residue was dissolved in ethanol (5 mL)
  6. stirringstirred at the same temperature for 14 hours
  7. customTo the resulting reaction solution
  8. extractionextracted with dichloromethane
  9. washThe dichloromethane layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-644c271d588b490597946888f3ccd869
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

Loading…