Ethanol → HCID 68802545, compound

Participants

Reaction Steps

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 (45 mg, 0.10 mmol), methylsulfonamide (12 mg, 0.12 mmol), triethylamine (0.021 mL, 0.15 mmol), and tetrahydrofuran (1.0 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (29 mg, 0.15 mmol) followed by 4-dimethylaminopyridine (15 mg, 0.12 mmol) at room temp. The reaction was stirred at room temp overnight. The reaction was concentrated and purified by reverse-phase HPLC (40 to 95% acetonitrile/water/0.05% trifluoroacetic acid) to give the title compound (yellow solid, 20.6 mg, 0.0394 mmol, 39% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70-0.92 (m, 1H), 1.72-1.89 (m, 1H), 2.84-3.04 (m, 2H), 3.35 (s, 3H), 3.98 (ddd, J=13.67, 10.94, 5.08 Hz, 1H), 5.95 (d, J=11.33 Hz, 1H), 6.65-7.58 (m, 6H), 7.67 (d, J=8.98 Hz, 1H), 7.75-7.89 (m, 2H), 8.16 (d, J=8.20 Hz, 1H), 12.17 (s, 1H). ES-MS m/z 523 (M+H).

Provenance & Evidence