Hydrochloric Acid → [4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 1804065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804065
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1.[OH-].[Na+].Cl.[CH3:22][C:23]1[C:24]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:25][CH:26]=[C:27]([CH3:29])[CH:28]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO.O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([N:33]2[CH2:34][CH2:35][N:30]([C:24]3[C:23]([CH3:22])=[CH:28][C:27]([CH3:29])=[CH:26][N:25]=3)[CH2:31][CH2:32]2)=[O:8])=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 584844961-(3,5-Dimethylpyridin-2-yl)piperazineHCID 58484624Methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate

Produkt 1

HCID 58484716[4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate (2 g) described in Preparation Example 116 were added 1N aqueous sodium hydroxide solution (9 mL) and methanol (18 mL), and the mixture was stirred at 60-70° C. 1N hydrochloric acid (9 mL) was added, a solution of 1-(3,5-dimethylpyridin-2-yl)piperazine (1.14 g) described in Preparation Example 47 in methanol (2 mL) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.65 g) were added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporation of the solvent, the residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (2.4 g).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0942c41825b241d28e1d6abbd6c64dda
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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