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Ethanol → HCID 86671731, Verbindung

HRID 2178707
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2178707
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:36](=[O:37])[N:11]3[CH2:12][CH2:13][N:14]([C@@H:17]([CH3:35])[CH2:18][O:19][C:20]4[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=4[S:29]([F:34])([F:33])([F:32])([F:31])[F:30])[C:15](=[O:16])[C:10]3=[CH:9][CH:8]=2)[CH:6]=1.C(O)C.[Cl-].[NH4+]>O.[Fe]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][C@@H:17]([N:14]2[CH2:13][CH2:12][N:11]3[C:36](=[O:37])[C:7]([N:5]4[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]4)=[CH:8][CH:9]=[C:10]3[C:15]2=[O:16])[CH3:35])=[C:21]([S:29]([F:30])([F:34])([F:33])([F:32])[F:31])[CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 86671730HCID 86671730, Verbindung

Produkt 1

HCID 86671731HCID 86671731, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 7-(4-methyl-1H-imidazol-1-yl)-2-{(2S)-1-[4-nitro-2-(pentafluoro-λ6-sulfanyl)phenoxy]propan-2-yl}-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione (C55) (790 mg, 1.44 mmol) and ethanol (10 mL) was heated to 55° C. Iron powder (99%, 243 mg, 4.31 mmol) and a solution of ammonium chloride (462 mg, 8.64 mmol) in water (2.5 mL) were added, and the reaction mixture was stirred at reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, concentrated in vacuo, treated with ethyl acetate and saturated aqueous sodium bicarbonate solution and filtered through Celite. The filter pad was rinsed with water and ethyl acetate; the organic portion of the filtrate was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification via silica gel chromatography (Gradient: 5% to 10% methanol in ethyl acetate) provided the product as a light yellow foam. Yield: 507 mg, 0.98 mmol, 68%. LCMS m/z 520.2 (M+1). 1H NMR (400 MHz, CDCl3), characteristic peaks: δ 1.48 (d, J=7.2 Hz, 3H), 3.71-3.79 (m, 1H) 3.85-3.92 (m, 1H), 4.05 (dd, J=9.6, 5.5 Hz, 1H), 4.99-5.08 (m, 1H), 6.80 (dd, half of ABX pattern, J=8.8, 2.6 Hz, 1H), 6.86 (br d, half of AB quartet, J=8.8 Hz, 1H), 7.06 (d, J=2.6 Hz, 1H).

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. temperatureto cool to room temperature
  3. concentrationconcentrated in vacuo
  4. additiontreated with ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. filtrationfiltered through Celite
  6. washThe filter pad was rinsed with water and ethyl acetate
  7. washthe organic portion of the filtrate was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification via silica gel chromatography (Gradient: 5% to 10% methanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0af8ba4e9b2745e0a6cd14a407349e14
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067934B2

Notizen zur Reaktion

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