Diisopropylethylamine → HCID 66969954, compound

HRID 1014063Notes

Reaction equation

HRID 1014063 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:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[NH:25][C:26](=[O:29])[CH2:27][CH3:28].C(N(C(C)C)CC)(C)C>C(O)C>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:16]([CH2:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[NH:25][C:26](=[O:29])[CH2:27][CH3:28])[CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66877517HCID 66877517, compound

Product 1

HCID 66969954HCID 66969954, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 3) A solution of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.88 g), N-[2-(aminomethyl)-4-chlorophenyl]propanamide hydrochloride obtained in Step 2 (1.99 g) and diisopropylethylamine (4.1 ml) in ethanol (15 ml) was stirred overnight at 70° C. The reaction solvent was evaporated under reduced pressure, the residue was dissolved in ethyl acetate and 1N sodium hydroxide, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. 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 further purified by HPLC. The obtained residue was extracted with ethyl acetate and saturated sodium hydrogen carbonate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol, and 4N hydrogen chloride-ethyl acetate solution was added. The precipitated crystals were collected by filtration, and recrystallized from ethanol and ethyl acetate to give the title compound (100 mg).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extraction1N sodium hydroxide, and the solution was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  9. customThe obtained residue was further purified by HPLC
  10. extractionThe obtained residue was extracted with ethyl acetate and saturated sodium hydrogen carbonate
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. customThe solvent was evaporated under reduced pressure
  15. dissolutionThe residue was dissolved in ethanol
  16. addition4N hydrogen chloride-ethyl acetate solution was added
  17. filtrationThe precipitated crystals were collected by filtration
  18. customrecrystallized from ethanol and ethyl acetate

Sources & evidence

ORD record
ord-4c29b32c4af64cdba60731776762547a
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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