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N-(6-Chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide → N-(6-(oxazol-2-yl)-5-(pyridin-4-yl)pyrazin-2-yl)cyclopropanecarboxamide

HRID 1710701
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1710701
[Cl-].[O:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Zn+].Cl[C:9]1[N:14]=[C:13]([NH:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[CH:12]=[N:11][C:10]=1[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:9]1[N:14]=[C:13]([NH:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[CH:12]=[N:11][C:10]=1[C:21]1[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 59457608N-(6-Chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamideHCID 178479834HCID 178479834, Verbindung2×

Produkt 1

HCID 16071780N-(6-(oxazol-2-yl)-5-(pyridin-4-yl)pyrazin-2-yl)cyclopropanecarboxamideAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator2×
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(1,3-Oxazol-2-yl)zinc chloride (0.33M in THF, 9.3 mL, 3.06 mmol) was added to a solution of N-(6-chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide (Preparation 8, 280 mg, 1.02 mmol) in THF (2 mL) and the mixture was degassed Pd(PPh3)4 (118 mg, 0.102 mmol, 10 mol %) was added and degassing was repeated. The reaction mixture was heated to 90° C. in a sealed tube and stirred overnight. The mixture was cooled and more (1,3-oxazol-2-yl)zinc chloride (0.33M, 5.0 mL, 1.65 mmol) and Pd(PPh3)4 (90 mg, 8 mol %) were added and the mixture was degassed and heated to 90° C. overnight. The reaction mixture was cooled and concentrated. The residue was purified by flash silica gel chromatography (dichloromethane/methanol 98:2) to give the title compound (80 mg, 26%) as a pale yellow solid.

Aufarbeitung

  1. additionwas added
  2. customdegassing
  3. temperatureThe mixture was cooled
  4. customthe mixture was degassed
  5. temperatureheated to 90° C. overnight
  6. temperatureThe reaction mixture was cooled
  7. concentrationconcentrated
  8. customThe residue was purified by flash silica gel chromatography (dichloromethane/methanol 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-7ea27d3422254ab0bdb0aa294d61ed73
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07790728B2

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