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Potassium Carbonate → Tert-butyl 4-(5-chloropyrazin-2-YL)piperazine-1-carboxylate

HRID 459868
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 459868
CN1C(=O)CCC1.Cl[C:9]1[CH:14]=[N:13][C:12]([Cl:15])=[CH:11][N:10]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:15][C:12]1[CH:11]=[N:10][C:9]([N:26]2[CH2:25][CH2:24][N:23]([C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:28][CH2:27]2)=[CH:14][N:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3362242,5-Dichloropyrazine

Produkt 1

HCID 22931015Tert-butyl 4-(5-chloropyrazin-2-YL)piperazine-1-carboxylateAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To an NMP (7.5 ml) solution of 1.51 g of 2,5-dichloropyrazine were added 2.00 g of 1-(t-butoxycarbonyl)piperazine and 2.00 g of potassium carbonate, followed by 1 hour of stirring under heating at 100° C. The mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 2.73 g of 2-chloro-5-(4-t-butoxycarbonylpiperazin-1-yl)pyrazine. Using this compound, 2-chloro-5-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}pyrazine was obtained in a similar manner to Example 14 as colorless crystals.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-1c01d216e0cd42eabb9a1cc79af91373
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07196080B2

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