Dimethyl Sulfoxide → HCID 178453635, Verbindung

HRID 1623273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623273
[Cl:1][C:2]1[C:3]([I:9])=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][CH2:12]1.CS(C)=O>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([I:9])=[CH:4][C:5]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:13][CH2:12]2)=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 218653365-Chloro-2-fluoro-4-iodopyridineHCID 178453642HCID 178453642, Verbindung

Produkt 1

HCID 178453635HCID 178453635, VerbindungAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 5-chloro-2-fluoro-4-iodopyridine (517 mg, 2.008 mmol), tert-butyl (trans-4-aminocyclohexyl)methylcarbamate (550 mg, 2.410 mmol), DMSO (2 ml) and TEA (0.336 ml, 2.410 mmol) reaction mixture was stirred at about 95° C. for about 26 hours. The crude reaction mixture was cooled to room temperature, mixed with 125 ml ethyl acetate, washed with saturated sodium bicarbonate (2×), water (3×), saturated salt solution (1×), dried sodium sulfate, filtered and concentrated under reduced pressure to yield a residue. The residue was purified by silica gel chromatography using a 40 g column, eluting from 0%-35% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, yielding 656 mg of titled compound as free base. LCMS (m/z): 466.1 (MH+), retention time=0.93 min.

Aufarbeitung

  1. customThe crude reaction mixture
  2. temperaturewas cooled to room temperature
  3. washwashed with saturated sodium bicarbonate (2×), water (3×), saturated salt solution (1×), dried sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a residue
  7. customThe residue was purified by silica gel chromatography
  8. washeluting from 0%-35% ethyl acetate with hexane
  9. concentrationThe desired fractions were concentrated to constant mass

Quellen und Nachweise

ORD-Eintrag
ord-657bc3ecb9604760a7858d6bdd0f9d61
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778951B2

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