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HCID 15544164, Verbindung → HCID 86671730, Verbindung

HRID 2178706
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2178706
CC(C)([O-])C.[K+].[OH:7][CH2:8][C@@H:9]([N:11]1[CH2:16][CH2:15][N:14]2[C:17](=[O:27])[C:18]([N:21]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]3)=[CH:19][CH:20]=[C:13]2[C:12]1=[O:28])[CH3:10].F[C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=1[S:39]([F:44])([F:43])([F:42])([F:41])[F:40]>O1CCCC1.O>[CH3:26][C:24]1[N:23]=[CH:22][N:21]([C:18]2[C:17](=[O:27])[N:14]3[CH2:15][CH2:16][N:11]([C@@H:9]([CH3:10])[CH2:8][O:7][C:30]4[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=4[S:39]([F:42])([F:43])([F:44])([F:40])[F:41])[C:12](=[O:28])[C:13]3=[CH:20][CH:19]=2)[CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 15544164HCID 15544164, VerbindungHCID 23665647Potassium tert-butoxideHCID 68379737HCID 68379737, Verbindung

Produkt 1

HCID 86671730HCID 86671730, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Versuchsvorschrift

A solution of potassium tert-butoxide in tetrahydrofuran (1 M, 1.97 mL, 1.97 mmol) was added to a slurry of 2-[(2S)-1-hydroxypropan-2-yl]-7-(4-methyl-1H-imidazol-1-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione (C54) (541 mg, 1.79 mmol) in tetrahydrofuran (6 mL), and the mixture was allowed to stir for 10 minutes. A solution of 1-fluoro-4-nitro-2-(pentafluoro-λ6-sulfanyl)benzene (P15) (478 mg, 1.79 mmol) in tetrahydrofuran (4 mL) was added, and the reaction mixture was stirred at room temperature for 18 hours. At that point, it was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Eluents: ethyl acetate, then 10% methanol in ethyl acetate) afforded the product as a yellow foam. Yield: 695 mg, 1.26 mmol, 70%. LCMS m/z 550.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.53 (d, J=7.1 Hz, 3H), 2.34 (d, J=1.0 Hz, 3H), 3.73-3.85 (m, 2H), 4.30-4.47 (m, 4H), 4.99-5.08 (m, 1H), 7.16-7.21 (m, 2H), 7.28 (d, J=7.7 Hz, 1H), 7.52 (d, J=7.7 Hz, 1H), 8.40 (dd, J=9.2, 2.7 Hz, 1H), 8.44 (br s, 1H), 8.71 (d, J=2.6 Hz, 1H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification via silica gel chromatography (Eluents

Quellen und Nachweise

ORD-Eintrag
ord-c862c129816148f7bcc8a48474c32a23
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067934B2

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