Triethylamine → HCID 54674187, compound

Participants

Reaction Conditions

Reaction Steps

N-[(3aR,4R,6aS)-4-methyloctahydrocyclopenta[c]pyrrol-4-yl]benzamide (118 mg, 0.483 mmol, Example 8) was combined with 2-bromo-6-(trifluoromethyl)pyridine (131 mg, 0.580 mmol) and triethylamine (0.202 mL, 1.449 mmol) in ethanol (0.2 mL). The reaction was heated at 75° C. for 72 hours. The reaction mixture was partitioned between water (1 mL) and dichloromethane. The crude brown material was purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane as eluent to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.71 (s, 1H), 8.16 (dd, J=5.3, 3.3, 2H), 7.47 (t, J=7.9, 1H), 7.43-7.30 (m, 3H), 6.96 (d, J=7.2, 1H), 6.46 (d, J=8.6, 1H), 3.79-3.64 (m, 2H), 3.60 (dd, J=11.1, 7.3, 1H), 3.56-3.45 (m, 2H), 2.80-2.69 (m, 1H), 2.25 (dd, J=21.5, 9.6, 1H), 2.00-1.78 (m, 2H), 1.64 (s, 3H), 1.45-1.33 (m, 1H); MS (ESI+) m/z 390 (M+H)+.

Provenance & Evidence