Reaktion #1583816

ord-6de36ca9f3f64dcf995d7a78c74a89df

Reaktionsgleichung

CCc1nc(-c2ccc(F)cc2)c(-c2ccnc(Cl)c2)s1
2-chloro-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine
NCc1ccccc1
benzylamine
CCc1nc(-c2ccc(F)cc2)c(-c2ccnc(NCc3ccccc3)c2)s1
N-Benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine

Reaktionsbedingungen

Temperatur
180°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenthe reaction mixture is concentrated under reduced pressure
  2. 2
    Filtrationthe resulting precipitate is filtered off
  3. 3
    Einengenthe filtrate is concentrated again
  4. 4
    SonstigeThe residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Vorschrift

With stirring, a mixture of 5.24 g (16.4 mmol) of 2-chloro-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine and 25 ml benzylamine is heated at 180° C. After 16 h, the reaction mixture is concentrated under reduced pressure, the residue is taken up in 100 ml of MTBE, the resulting precipitate is filtered off and the filtrate is concentrated again. The residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 4.75 g (88%) of the desired product; 1H-NMR(MeCN-d3) δ: 7.91 (d, 1H), 7.49 (m, 2H), 7.29 (m, 5H), 7.07 (m, 2H), 6.45 (d, 1H), 6.39 (s, 1H), 5.83 (br.s, 1H), 4.43 (d, 2H), 3.02 (q, 2H), 1.38 (t, 3H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09198426B2uspto-grants-2015_12