Triethylamine → HCID 66969600, compound

HRID 1014064Notes

Reaction equation

HRID 1014064 reaction equation
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[NH2:16][CH2:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:27])[CH3:26])[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C>CO>[ClH:12].[C:25]([NH:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:16]1[CH:10]=[C:11]([Cl:12])[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1]1=[NH:2])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 2760945N-[3-(aminomethyl)phenyl]acetamide Hydrochloride

Product 1

HCID 66969600HCID 66969600, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.70 g) and N-[3-(aminomethyl)phenyl]acetamide hydrochloride (1.20 g) in methanol (10 ml) was added triethylamine (1.66 ml) at room temperature, and the mixture was stirred overnight at 50° C. The reaction solvent was evaporated under reduced pressure, acetic acid (10 ml) was added, and the mixture was stirred at 50° C. for 2 hr. The solvent was evaporated under reduced pressure, ethyl acetate and saturated aqueous sodium hydrogen carbonate were added, and the aqueous layer was basified with 1N aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). The obtained residue was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (1 ml) was added, and the mixture was crystallized from methanol-ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized from methanol-ethyl acetate to give the title compound (0.30 g).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure, acetic acid (10 ml)
  2. additionwas added
  3. stirringthe mixture was stirred at 50° C. for 2 hr
  4. customThe solvent was evaporated under reduced pressure, ethyl acetate and saturated aqueous sodium hydrogen carbonate
  5. additionwere added
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  10. dissolutionThe obtained residue was dissolved in methanol
  11. addition4N hydrogen chloride-ethyl acetate solution (1 ml) was added
  12. customthe mixture was crystallized from methanol-ethyl acetate
  13. filtrationThe precipitated crystals were collected by filtration
  14. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-74322630f2de47b9a10b5ed0e97f3013
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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