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Ammonia → 2-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-5-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzonitrile

HRID 2411850
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2411850
Br[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][S:10]2(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]=1[C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][N:25]=2)[CH2:20][CH2:19]1)=[O:17].O.N.[CH3:34][N:35](C)C=O>[C-]#N.[Zn+2].[C-]#N>[CH3:30][C:29]1[C:24]([N:21]2[CH2:22][CH2:23][N:18]([C:16]([C:3]3[CH:4]=[CH:5][C:6]([CH2:8][N:9]4[CH2:13][CH2:12][CH2:11][S:10]4(=[O:15])=[O:14])=[CH:7][C:2]=3[C:34]#[N:35])=[O:17])[CH2:19][CH2:20]2)=[N:25][CH:26]=[C:27]([CH3:31])[CH:28]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 962WaterHCID 6228DimethylformamideHCID 71252686[2-Bromo-4-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Produkt 1

HCID 712526912-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-5-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Under a nitrogen stream, [2-bromo-4-(1,1-dioxo-1λ6-isothiazolidin-2-ylmethyl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (120 mg) described in Example 461 was dissolved in N,N-dimethylformamide (5 mL), zinc cyanide (28 mg) and tetrakistriphenylphosphine palladium(0)(55 mg) were added, and the mixture was stirred at 130° C. for 4 hr. After completion of the reaction, to the reaction mixture was added water/saturated aqueous ammonium chloride solution/28% aqueous ammonia (4:4:1), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (68 mg).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4e111eeb38224b27a6e53fee4b6d6729
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08816079B2

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