Reaction Steps
2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (77 mg, 0.24 mmol) was added to a solution of (±)-(3RS,3aRS)-2-(3-chloro-4-cyanophenyl)-3-(4-fluorophenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 2 (89 mg, 0.20 mmol), triethylamine (0.056 mL, 0.40 mmol), and dimethylformamide (2.0 mL) at room temp. After 10 minutes, 2-(pyrrolidin-1-yl)ethanamine (0.051 mL, 0.40 mmol) was added. After 40 minutes, the reaction was quenched with 0.30 mL 3N hydrogen chloride and purified by reverse-phase HPLC (20 to 90% acetonitrile/water/0.05% trifluoroacetic acid). The purified fractions were combined, neutralized with saturated sodium bicarbonate solution, and concentrated until a precipitate formed. The precipitate was filtered, washed with water, and dried to give the title compound (yellow solid, 45.5 mg, 0.084 mmol, 42% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.80 (m, 1H), 1.64 (m, 4H), 1.79 (m, 1H), 2.46 (m, 4H), 2.54 (t, J=7.03 Hz, 2H), 2.91 (m, 2H), 3.35 (q, J=6.64 Hz, 2H), 3.95 (ddd, J=13.57, 11.03, 5.08 Hz, 1H), 5.92 (d, J=11.33 Hz, 1H), 7.15 (m, 6H), 7.65 (d, J=8.59 Hz, 1H), 7.69 (s, 1H), 7.75 (dd, J=8.20, 1.56 Hz, 1H), 8.10 (d, J=8.20 Hz, 1H), 8.47 (t, J=5.86 Hz, 1H). ES-MS m/z 542 (M+H).
