Hydrochloric Acid → HCID 86671244, compound

HRID 884130Notes

Reaction equation

HRID 884130 reaction equation
[CH:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=O.Cl.[CH2:28]([O:30][C:31](=[O:34])[CH2:32][NH2:33])[CH3:29].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].Cl>CO>[CH2:28]([O:30][C:31](=[O:34])[CH2:32][NH:33][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)=[CH:10][N:9]=2)=[CH:25][CH:26]=1)[CH3:29]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 86616533HCID 86616533, compound

Product 1

HCID 86671244HCID 86671244, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[2-(4-formylphenoxy)-5-pyridyl]-3,4-dichlorobenzamide (1.00 g, 2.58 mmol), glycine ethyl ester hydrochloride (0.400 g, 2.84 mmol) and sodium acetate (0.230 g, 2.84 mmol) in methanol (20 mL) was stirred for 30 minutes at 60° C. The reaction solution was cooled with ice, and then sodium cyanoborohydride (0.180 g, 2.84 mmol) was added. The resulting solution was stirred at the same temperature for 1 hour. To the reaction solution was added 5 M hydrochloric acid (2 mL) and concentrated under reduced pressure. To the residue was added a saturated sodium bicarbonate solution, and extracted with dichloromethane. The dichloromethane layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2), to thereby yield 0.752 g of the title compound.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added a saturated sodium bicarbonate solution
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-d14fc723025b4ded98f8668a23b29ccb
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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