Reaktion #2257340

Reaktionsgleichung

ethyl 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinate

ammonia

→

5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinamide

Ausbeute 86.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe tube was sealed
2. 2
   Sonstigewas opened at −40° C.
3. 3
   Sonstigeto rise to ambient temperature
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Sonstigeto give a residue which
6. 6
   Sonstigewas purified by preparative HPLC (Condition B-58 as described in general methods)

Vorschrift

A solution of ethyl 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinate (0.100 g, 0.222 mmol) in ethanol (10 mL) was purged with ammonia gas at −40° C. in a sealed tube for 15 min. The tube was sealed and the reaction mixture was stirred at ambient temperature for 14 h. The sealed tube was opened at −40° C. and allowed to rise to ambient temperature. The solvent was evaporated under reduced pressure to give a residue which was purified by preparative HPLC (Condition B-58 as described in general methods) to get 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinamide (80.0 mg, 86.0%) as a white solid. LCMS Condition B-26: retention time 2.28 min, [M+1]=421.2. HPLC Condition B-6: retention time 7.62 min, purity 99.33%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.84 (d, J=4.0 Hz, 2H), 6.68 (t, J=4.0 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H), 7.25-7.32 (m, 1H), 7.34-7.41 (m, 5H), 7.45-7.48 (m, 2H), 7.52-7.54 (m, 2H), 7.67 (s, 1H), 7.93 (d, J=4.0 Hz, 1H), 8.32 (s, 1H), 8.95 (t, J=4.0 Hz, 1H), 9.11 (d, J=2.4 Hz, 1H), 9.46 (d, J=2.0 Hz, 1H).

Quelle