Reaktion #1179389

Reaktionsgleichung

(R)-2-(5-amino-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyridin-2-ylamino)-2-(4-fluorophenyl)ethanol

formamidine acetate

NaHCO3

EtOAc

→

title compound

Ausbeute 153.0%

(2R)-2-(1-(5-Cyclopropyl-1H-pyrazol-3-yl)-1H-imidazo[4,5-c]pyridin-6-ylamino)-2-(4-fluorophenyl)ethanol

Ausbeute 153.0%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 2 hours
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with brine (10 ml)
5. 5
   Trocknendried over sodium sulfate
6. 6
   SonstigeThe solvent was removed under reduced pressure
7. 7
   Sonstigethe residue was purified by column chromatography (EtOAc-MeOH=20:1)

Vorschrift

A mixture of (R)-2-(5-amino-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyridin-2-ylamino)-2-(4-fluorophenyl)ethanol (Method 93, 0.14 g, 0.38 mmol) and formamidine acetate (0.079 g, 0.76 mmol) in EtOH (5 ml) was heated at reflux for 2 hours. After cooling to 25° C., the reaction mixture was treated with saturated NaHCO3 solution (10 ml) and EtOAc (30 ml). The organic layer was separated, washed with brine (10 ml), and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (EtOAc-MeOH=20:1) to give the title compound as an off-white solid (0.22 g, 32%). 1H NMR (400 MHz) 12.76 (s, 1H), 8.40 (s, 1H), 8.34 (s, 1H), 7.43 (m, 2H), 7.10 (m, 2H), 6.92 (s, 1H), 6.72 (d, J=7.2 Hz, 1H), 6.25 (s, 1H), 4.92 (m, 2H), 3.62 (m, 2H), 1.97 (m, 1H), 1.02 (m, 2H), 0.77 (m, 2H). MS: Calcd.: 378; Found: [M+H]+ 379.

Quelle