Ammonium Acetate → 2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-oxo-4-phenylbutyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one (1.56 g, 1 eq.) in acetic acid (10 mL) was added ammonium acetate (3.37 g, 10 eq.). The reaction was stirred at 120° C. for 8 hours. The reaction mixture was poured onto water (100 mL) and extracted with dichloromethane (3×100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (0-10% methanol in dichloromethane) gave the 2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.374 g, 27%). 1H NMR (CDCL3) 400 MHz δ 8.08 (dd, JA=4.8 Hz, JB=1.6 Hz, 1H), 7.97 (dd, JA=8.0 Hz, JB=1.2 Hz, 1H), 7.46 (dd, JA=8.0 Hz, JB=1.6 Hz, 1H), 7.34-7.15 (m, 6H), 7.08 (td, JA=7.6 Hz, JB=1.2 Hz, 1H), 6.98 (dd, JA=7.6 Hz, JB=4.8 Hz, 1H), 6.86 (dd, JA=7.6 Hz, JB=0.8 Hz, 1H), 6.81 (s, 1H), 6.27 (s, 1H), 3.07-2.90 (m, 4H); LCMS: 339 [M+H].

Provenance & Evidence