Ammonia → HCID 18391707, compound

Participants

Reaction Steps

A solution of HCl in ether was added dropwise to a stirred solution of compound 24b (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 223-225° C. MS m/e (DCI/NH3): 207 (M+H+). 1H NMR (DMSO-d6, 300 MHz) δ: 8.65 (d, J=2.9 Hz, 1H), 8.46 (d, J=5.9 Hz, 1H), 8.00 (dd, J=2.3, 8.7 Hz, 1H), 7.81 (dd, J=5.2, 8.7 Hz, 1H), 4.60 (dd, J=8.1, 11.0 Hz, 1H), 4.49 (dd, J=3.5, 10.4 Hz, 1H), 4.04-3.95 (m, 1H), 3.64-3.58 (m, 1H), 2.92 (s, 3H), 2.80-2.74 (m, 1H), 2.45-2.40 (m, 1H), 2.04-1.98 (m, 1H), 1.95-1.89 (m, 1H), 1.07 (d, J=6.9 Hz, 3H). Anal. Calc. for C12H18N2O.2.0 HCl: C, 51.62; H, 7.22; N, 10.03. Found: C, 51.84; H, 7.36; N, 9.90. [α]D =-2.3° (c=0.32, MeOH).

Provenance & Evidence