Triethylamine → HCID 54675117, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared by combining (3aS,4S,6aS)—N-(3-fluorophenyl)octahydrocyclopenta[c]pyrrole-4-carboxamide (98 mg, 0.395 mmol) from Example 55, 2-bromo-6-(trifluoromethyl)pyridine (125 mg, 0.553 mmol), and triethylamine (0.165 mL, 1.184 mmol) in ethanol (0.2 mL). The reaction mixture was heated at 80° C. for 72 hours. The reaction was quenched with water (1 mL) and the resulting brown oil was purified using a 12 g silica gel cartridge eluting with 1-100% ethyl acetate/hexanes over 20 minutes to give a solid. The solid was recrystallized from ethyl acetate/heptane (10%) to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 11.06 (s, 1H), 8.21 (dt, J=11.7, 2.2, 1H), 7.60-7.59 (m, 1H), 7.54-7.47 (m, 1H), 7.30 (td, J=8.2, 6.8, 1H), 6.98 (d, J=7.3, 1H), 6.91 (tdd, J=8.6, 2.6, 0.6, 1H), 6.41 (d, J=8.6, 1H), 3.46 (dd, J=10.3, 7.6, 3H), 3.23-3.14 (m, 1H), 3.06 (dd, J=10.8, 5.7, 1H), 2.90-2.72 (m, 2H), 2.22-2.12 (m, 1H), 2.12-1.95 (m, 2H), 1.39 (dtd, J=10.4, 8.0, 5.4, 1H); MS (ESI+) m/z 394 (M+H)+.

Provenance & Evidence