Reaktion #163055

Reaktionsgleichung

2-Chloro-5-fluoro-6-(5-isopropoxy-1H-pyrazol-3-ylamino)nicotinonitrile

(S)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)nicotinamide

(S)-1-(4-fluorophenyl)ethanamine

DIEA

n-BuOH

→

title compound

Ausbeute 48.0%

(S)-5-Fluoro-2-(1-(4-fluorophenyl)ethylamino)-6-(5-isopropoxy-1H-pyrazol-3-ylamino)nicotinonitrile

Ausbeute 48.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 25° C.
2. 2
   Einengenconcentrated
3. 3
   SonstigeThe resulting residue was purified by column chromatography (DCM-MeOH=80:1)

Vorschrift

2-Chloro-5-fluoro-6-(5-isopropoxy-1H-pyrazol-3-ylamino)nicotinonitrile (Method 2; 1.4 g, 5.0 mmol) and (S)-1-(4-fluorophenyl)ethanamine (1.0 g, 9.0 mmol) were added to a solution of n-BuOH (8 ml) and DIEA (0.8 g, 6.0 mmol) in a sealed tube. The reaction was heated to 135° C. for 48 hrs, cooled to 25° C., and concentrated. The resulting residue was purified by column chromatography (DCM-MeOH=80:1) to give the title compound (0.90 g, 48%). 1H NMR (400 MHz, CD3OD) δ 7.43 (d, J=10.5 Hz, 1H), 7.39-7.35 (m, 2H), 7.04-6.99 (m, 2H), 5.47 (s, 1H), 5.12-5.11 (m, 1H), 4.60-4.51 (m, 1H), 1.56 (d, J=7.0 Hz, 3H), 1.33-1.30 (m, 6H). MS: Calcd.: 398. Found: [M+H]+ 399.

Quelle