Methyl morpholine oxide → (4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone

HRID 597868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597868
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:14]3[N:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]3=[N:12][C:11]=2[CH3:20])=[O:9])=[C:4]([F:21])[CH:3]=1.[CH3:22][N+:23]1([O-])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CC(CC(C)=O)=O.CC(CC(C)=O)=O.O=[V].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:14]3[N:15]=[C:16]([Cl:19])[CH:17]=[C:18]([CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:13]3=[N:12][C:11]=2[CH3:20])=[O:9])=[C:4]([F:21])[CH:3]=1

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 56954583(4-Chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone

Produkt 1

HCID 56954584(4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 407389Vanadium oxyacetoacetonateKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Add ethanol (12 L), (4-chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone (897.70 g, 2.77 mol) and bis(2,4-pentanedionato)oxovanadium (IV) (146.81 g, 553.67 mmol) to a reaction vessel with a nitrogen atmosphere. Add an ethanol (6 L) solution of 4-methylmorpholine 4-oxide (3.89 kg, 33.21 mol) drop-wise over 150 min keeping the reaction temperature at 23-33° C.; then heat the reaction at 40° C. for 48 h. Cool the reaction and concentrate by removal of solvent (13 L). Filter the resulting mixture, rinse the filter cake with hexane (1 L) and then dry. (728 g, 66.25%; mp 145-147° C.; M+=423).

Aufarbeitung

  1. customat 23-33° C.
  2. temperaturethen heat
  3. customthe reaction at 40° C. for 48 h
  4. temperatureCool
  5. customthe reaction
  6. concentrationconcentrate by removal of solvent (13 L)
  7. filtrationFilter the resulting mixture
  8. washrinse the filter cake with hexane (1 L)
  9. customdry

Quellen und Nachweise

ORD-Eintrag
ord-d29f2af9e9ac4fc9a8153462fdecc538
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897600B2

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