StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dichloromethane → 4-Phenyl-1-{[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-7-yl]methyl}pyrrolidin-2-one

HRID 2043688
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2043688
Cl.[NH2:2][CH2:3][CH:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][C:6]([O:8]C)=O.[F:16][C:17]([F:30])([F:29])[C:18]1[N:22]2[N:23]=[CH:24][C:25]([CH:27]=O)=[CH:26][C:21]2=[N:20][N:19]=1.C(N(CC)CC)C.ClCCl>ClC(Cl)C.COCCOC>[C:10]1([CH:4]2[CH2:3][N:2]([CH2:27][C:25]3[CH:24]=[N:23][N:22]4[C:18]([C:17]([F:30])([F:16])[F:29])=[N:19][N:20]=[C:21]4[CH:26]=3)[C:6](=[O:8])[CH2:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 536292043-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine-7-carbaldehydeHCID 68748102Methyl 4-amino-3-phenylbutanoate hydrochloride

Produkt 1

HCID 577430604-Phenyl-1-{[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-7-yl]methyl}pyrrolidin-2-oneAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
11 °C

Versuchsvorschrift

Methyl 4-amino-3-phenylbutanoate hydrochloride x11 (0.19 g, 0.83 mmol, 1.05 eq) is added to a solution of aldehyde x235 (0.17 g, 0.79 mmol) in dry dichloroethane (DCE) (7.8 ml). The mixture is kept at room temperature for 30 min, cooled to 10-12° C., and a solution of triethylamine (0.15 ml, 0.83 mmol, 1.05 eq) in dry DME (2.5 ml) is added dropwise. The mixture is additionally stirred at the same temperature for 1 h and cooled to 0-5° C. Then STAB (0.23 g, 1.10 mmol, 1.4 eq) is added in portions under vigorous stirring. The mixture is additionally stirred at 0-5° C. for 30 min and kept at room temperature overnight. Then the mixture is heated to 60° C. for 2 h and cooled to room temperature. An equal volume of dichloromethane is added, and the mixture is washed with 10% K2CO3 (2×10 ml). The mixture is dried over anhydrous Na2SO4 and evaporated. The oily residue is triturated with ether, and the formed crystals are separated by filtration, washed twice with ether, and vacuum-dried to give white fine-crystalline 4-phenyl-1-{[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-7-yl]methyl}pyrrolidin-2-one 255.

Aufarbeitung

  1. temperaturecooled to 0-5° C
  2. additionThen STAB (0.23 g, 1.10 mmol, 1.4 eq) is added in portions under vigorous stirring
  3. stirringThe mixture is additionally stirred at 0-5° C. for 30 min
  4. waitkept at room temperature overnight
  5. temperatureThen the mixture is heated to 60° C. for 2 h
  6. temperaturecooled to room temperature
  7. washthe mixture is washed with 10% K2CO3 (2×10 ml)
  8. dry with materialThe mixture is dried over anhydrous Na2SO4
  9. customevaporated
  10. customThe oily residue is triturated with ether
  11. customthe formed crystals are separated by filtration
  12. washwashed twice with ether
  13. customvacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-722b5906cf88408cac3effb8bac4cc67
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586623B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion