Reacción #1583816

ord-6de36ca9f3f64dcf995d7a78c74a89df

Ecuación de reacción

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

Condiciones de reacción

Temperatura
180°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09198426B2uspto-grants-2015_12