Ammonia → HCID 18391710, compound

Participants

Reaction Steps

A solution of hydrochloride in ether was added dropwise to a stirred solution of compound 25b (55 mg, 0.27 mmol) in diethyl ether at room temperature. The resultant white precipitate was then collected by centrifugation and triturated with three portions of diethyl ether. The hygroscopic solid was obtained in 56% yield (42 mg). mp 219-220° C. MS m/e (DCI/NH3): 221 (M+H+). 1H NMR (D2O, 300 MHz) δ: 8.45 (d, J=2.6 Hz, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.91 (m, 1H), 7.76 (dd, J=5.2, 8.8 Hz, 1H), 4.59 (dd, J=2.9, 11.0 Hz, 1H), 4.43 (dd, J=5.9, 11.0 Hz, 1H), 4.04-3.95 (m, 1H), 4.08-4.00 (m, 1H), 3.83 (dd, J=6.6, 11.0 Hz), 3.05 (s, 3H), 2.95 (t, J=11.0 Hz, 1H), 2.45-2.00 (m, 2H), 2.14-2.03 (m, 1H), 1.60-1.45 (m, 2H), 0.94 (t, J=7.4 Hz, 3H). Anal, Calcd. for C13H20N2O.1.9 HCl: C, 53.92; H, 7.62; N, 9.67. Found: C, 54.00; H, 7.59; N, 9.35. [α]D =-1.9° (c 0.37, MeOH).

Provenance & Evidence