Phenacylamine → HCID 67540673, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% in mineral oil, 0.099 g, 2.46 mmol) in DMF (5 mL) was added cinnolin-4-ol (prepared from 2-aminoacetophenone according to the procedures described in U.S. Pat. No. 4,620,000), 0.300 g, 2.05 mmol) in DMF (2 mL) dropwise. The reaction mixture was warmed at 40° C. and stirred for 30 minutes. After cooling, N-phenyltrifluoromethanesulfonimide (0.880 g, 2.46 mmol) in DMF (2 mL) was added, and the reaction mixture was stirred at room temperature for 1 hour. 1-Boc piperazine (0.765 g, 4.11 mmol) was added to the mixture. The reaction was stirred at 80° C. for 4 hours. After cooling, the mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with water, brine, dried and concentrated. The residue was purified by column chromatography (1:1 to 1:3 hexanes/EtOAc) to give 4-Cinnolin-4-yl-piperazine-1-carboxylic acid tert-butyl ester (0.246 g, 38%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 8.91 (s, 1H), 8.47 (d, J=8.4 Hz, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.80 (t, J=7.2 Hz, 1H), 7.69 (t, J=7.2 Hz, 1H), 3.74 (m, 4H), 3.34 (m, 4H), 1.51 (s, 9H). LCMS (APCI+) m/z 315 [M+H]+; Rt=2.14 minutes.

Provenance & Evidence