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(6-Methoxypyridin-3-yl)boronic acid → HCID 25093775, Verbindung

HRID 600284
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600284
Cl[C:2]1[N:24]=[CH:23][C:5]2[N:6]=[C:7]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:8](=[O:16])[N:9]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15])[C:4]=2[CH:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][N:28]=1>O1CCOCC1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:25][O:26][C:27]1[N:28]=[CH:29][C:30]([C:2]2[N:24]=[CH:23][C:5]3[N:6]=[C:7]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:8](=[O:16])[N:9]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH3:15])[C:4]=3[CH:3]=2)=[CH:31][CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 45379959HCID 45379959, Verbindung

Produkt 1

HCID 25093775HCID 25093775, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittel
HCID 10340
Sodium Carbonate
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 7-chloro-3-(piperazin-1-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one (72 mg, 0.18 mmol) in 1,4-dioxane (2.5 mL) was treated with tetrakis(triphenylphosphine) palladium(0) (19 mg, 0.016 mmol, Strem) and stirred at room temperature for five minutes. A warm solution of 2-methoxy-5-pyridineboronic acid (41 mg, 0.27 mmol, Frontier) in ethanol (0.5 mL) and 2.0 M aqueous sodium carbonate 1.5 mL) were added. The mixture was refluxed for 2.0 hours, filtered hot through celite and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, concentrated under reduced pressure, and passed through a column of silica gel with 2% methanol/dichloromethane. Fractions were concentrated at reduced pressure and triturated with diethyl ether. The 7-(6-methoxypyridin-3-yl)-3-(piperazin-1-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one was obtained as a pink powder.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2.0 hours
  2. filtrationfiltered hot through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. concentrationFractions were concentrated at reduced pressure
  11. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5fb95dba63aa46089b548a9e7bdfec0d
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902195B2

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