Reaktion #1151609

Reaktionsgleichung

N-{2-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide

ammonium acetate

NH4OH

→

NH4OH

N-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide

Ausbeute 146.6%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was sealed
2. 2
   Sonstigeto give a viscous oil
3. 3
   Temperaturheating
4. 4
   TemperaturThe reaction mixture was cooled
5. 5
   ExtraktionThe mixture was then extracted with CHCl3 (3×)
6. 6
   WaschenThe combined organic portions were washed with brine
7. 7
   Trocknendried with Na2SO4
8. 8
   Einengenconcentrated

Vorschrift

A pressure flask was charged with N-{2-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide (980 mg, 2.39 mmol) and ammonium acetate (1.25 g). The flask was sealed and heated to 160° C. The solids soon melted to give a viscous oil and heating was continued for 24 h. The reaction mixture was cooled and treated with H2O and NH4OH solution until pH reached ˜12. The mixture was then extracted with CHCl3 (3×). The combined organic portions were washed with brine, dried with Na2SO4 and concentrated. Column chromatography (SiO2, 5% MeOH/CHCl3 saturated with NH4OH) gave N-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide (584 mg) as a tan foam. MS m/z 334 (M+H). 1H NMR (300 MHz, CDCl3) δ 5.57 (s, 1H), 4.92 (s, 2H), 4.77 (s, 2H), 4.71 (br s, 2H), 3.62 (q, J=7.0 Hz, 2H), 2.44 (s, 6H), 1.96 (s, 3H), 1.30 (s, 6H), 1.24 (t, J=7.0 Hz, 3H).

Quelle