Triethylamine → 6-CHLOROPYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYL-2-HYDROXYETHYL)AMIDE

HRID 2056411

Reaktionsgleichung

Reaktionsgleichung von HRID 2056411
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:15][CH2:16][CH:17]([CH:19]1[CH2:21][CH2:20]1)[OH:18].C(N(CC)CC)C>O1CCOCC1.O>[CH:19]1([CH:17]([OH:18])[CH2:16][NH:15][C:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])[CH2:21][CH2:20]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 64157626-chloropyridazine-3-carboxylic AcidHCID 148520982-Amino-1-cyclopropylethan-1-ol

Produkt 1

HCID 632963846-CHLOROPYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYL-2-HYDROXYETHYL)AMIDEAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To the solution of 6-chloropyridazine-3-carboxylic acid (375 mg, 2.37 mmol) in 5 mL of dioxane was added thionyl chloride (420 mg, 3.56 mmol). The mixture was refluxed for 4 hours and the solvent was removed in vacuo. 2-Amino-1-cyclopropylethanol (479 mg, 4.73 mmol) in 5 mL of dioxane was added to the residue and followed by the addition of triethylamine (0.2 mL). The mixture was stirred at ambient temperature overnight. Water was added to the mixture and then extracted with ethyl acetate. The organic extract was separated, washed with water and brine; dried over Na2SO4. The residue after removal of solvent was purified by column chromatography eluted with ethyl acetate:hexane (70:30) to yield 58 mg of the white desired product.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 4 hours
  2. customthe solvent was removed in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. customwas separated
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. customThe residue after removal of solvent
  9. customwas purified by column chromatography
  10. washeluted with ethyl acetate:hexane (70:30)

Quellen und Nachweise

ORD-Eintrag
ord-48754c990b3e4ebb9934d80d5c9146ed
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335658B2

Verknüpfte Notizen

Wird geladen…