Reaktion #85077

ord-9812e37926574f169fb20e859947b936

Reaktionsgleichung

COc1cn(C(CC(F)(F)F)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4,4-trifluorobutanoic acid
CCOC(=O)c1ccc(N)cc1
ethyl 4-aminobenzoate
CC(C)N=C=NC(C)C
DIC
CCOC(=O)c1ccc(NC(=O)C(CC(F)(F)F)n2cc(OC)c(-c3cc(Cl)ccc3C#N)cc2=O)cc1
Ethyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4,4-trifluorobutanoyl}amino)benzoate

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction product was purified by preparative HPLC [column
  2. 2
    Sonstigea further 3 min 90% acetonitrile

Vorschrift

63.0 mg (157 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4,4,4-trifluorobutanoic acid (racemate), 26.0 mg (157 μmol) of ethyl 4-aminobenzoate, 22.3 mg (157 μmol) of Oxima and 24.0 μl (157 μmol) of DIC in 1.6 ml of dimethylformamide were reacted according to General Method 5B. The reaction product was purified by preparative HPLC [column: Chromatorex C18, 10 μm, 125×30 mm, mobile phase: acetonitrile/0.05% formic acid gradient (0 to 3 min 10% acetonitrile, to 35 min 90% acetonitrile and a further 3 min 90% acetonitrile)]. Yield: 25.1 mg (28% of theory)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434690B2uspto-grants-2016_09