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Ethyl Acetate → HCID 178452597, Verbindung

HRID 2064435
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2064435
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([C:19]3([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].[C:37](N1C=CN=C1)(N1C=CN=C1)=[O:38].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCOCC1>[OH:38][C:37]1[N:12]2[C:3]([C:4]3[CH:5]=[C:6]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:7]([C:13]4[CH:18]=[CH:17][C:16]([C:19]5([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]5)=[CH:15][CH:14]=4)=[N:8][C:9]=3[CH:10]=[CH:11]2)=[N:1][N:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 57805468Tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate

Produkt 1

HCID 178452597HCID 178452597, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a round bottom flask was added tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (1-6) (2.77 g, 5.75 mmol), and 1,1′-carbonylbis(1H-imidazole) (4.10 g, 4.40 mmol), in 1,4 Dioxane (30 mL). The sealed reaction mixture was then heated at 95° C. under an atmosphere of nitrogen. To the crude reaction mixture was added a saturated solution of sodium bicarbonate (100 mL) and ethyl acetate. The organic layer was washed with a saturated solution of sodium bicarbonate, followed by water, then brine, dried over sodium sulfate, filtered, and concentrated. The resulting residue was then purified by silica gel chromatography eluting with 0-10% IPA/DCM. The appropriate fractions were then combined and the solvent was removed in vacuo to give tert-butyl {1-[4-(3-hydroxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (1-6a) as a tan solid. MS (M+H)+: observed=508.1, calculated=508.6.

Aufarbeitung

  1. customThe sealed reaction mixture
  2. customTo the crude reaction mixture
  3. washThe organic layer was washed with a saturated solution of sodium bicarbonate
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was then purified by silica gel chromatography
  8. washeluting with 0-10% IPA/DCM
  9. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8a26d54978b04f44920e8a749d8221a4
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08288407B2

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