Diisopropylethylamine → HCID 11965781, Verbindung

HRID 1441642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441642
CO[C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[N:12][CH:11]=2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH2:20].ClC([O:25][C:26]1C=CC(Cl)=CC=1)=O.[CH3:33][S:34]([NH:37][NH2:38])(=[O:36])=[O:35].CCN(C(C)C)C(C)C>O1CCOCC1>[O:25]=[C:26]1[N:38]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])[C:3](=[O:21])[C:4]2[C:5](=[CH:6][C:7]([C:16]([F:19])([F:18])[F:17])=[C:8]([C:10]3[CH:15]=[CH:14][N:13]=[N:12][CH:11]=3)[CH:9]=2)[NH:20]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 269268MethanesulfonohydrazideHCID 11965780HCID 11965780, Verbindung

Produkt 1

HCID 11965781HCID 11965781, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution containing 2-amino-5-pyridazin-4-yl-4-trifluoromethyl-benzoic acid methyl ester (65.5 mg, 0.22 mmol) and 4-chlorophenyl chloroformate (34 μL, 0.24 mmol) in dioxane (3 mL) was heated at 80° C. for 1.5 h. After allowing the reaction mixture to cool down to r.t., CH3SO2NHNH2 (48.5 mg, 0.44 mmol) and i-Pr2NEt (38.5 μL, 0.22 mmol) were added. The mixture was heated to 80° C. for 1 h and, after cooling to r.t., the solvent was removed in vacuo. The residue was dissolved in DCM and the product was precipitated by addition of Et2O. Filtration and drying provided the title product (34.4 mg, 39%) as a white solid. API-ES: m/z 402 [M+H]+, rt 2.02 min.

Aufarbeitung

  1. temperatureto cool down to r.t.
  2. temperatureThe mixture was heated to 80° C. for 1 h
  3. temperatureafter cooling to r.t.
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in DCM
  6. customthe product was precipitated by addition of Et2O
  7. filtrationFiltration
  8. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-e54701e7ad4645d5a6590bc66afa6f6a
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655666B2

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