Pyridine → HCID 136397084, compound

Participants

Reaction Steps

To a solution of Example 83B (50 mg, 0.09 mmol) in dichloromethane (350 μL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (15 μL, 0.14 mmol) and triethylamine (27 μL, 0.19 mmol) and stirring was continued at 0° C. for 1 hour. Triethylamine (19 uL, 0.14 mmol) was added and the solution was warmed to room temperature over 1 hour. 2-chloro-1-ethanesulfonyl chloride (15 μL, 0.14 mmol) and triethylamine (19 μL, 0.14 mmol) were added and stirring continued for 30 minutes. The solution was diluted with dichloromethane (5 mL) and the solution washed with brine (1×5 mL), dried (Na2SO4), the drying agent filtered off and the solvent removed in vacuo. The crude residue was dissolved in tetrahydrofuran (350 μL) and morpholine (16 μL, 0.19 mmol) was added, the solution stirred at room temperature for 16 hours and the solvent removed in vacuo. The crude residue was dissolved in 4M HCl in dioxane (4 mL) and the solution stirred at room temperature for 1 hour. Solvent was removed in vacuo and the crude residue was dissolved in dichloromethane (2 mL) and pyridine (111 μL, 1.4 mmol) and methanesulfonyl chloride (15μL, 0.19 mmol) were added and the solution stirred at room temperature for 16 hours. The sovent was removed in vacuo and the crude residue was purified by column chromatography on silica gel (2-10% methanol/chloroform) to yield the title compound as a colorless solid (58 mg, 91%); 1H NMR (d6-DMSO) δ 15.25 (s, 1H), 8.01, 7.99 (d, 1H), 7.61, 7.59 (d, 2H), 7.53-7.28 (m, 5H), 3.70-3.64 (m, 2H), 3.62-3.49 (m, 5H), 3.10-3.01 (m, 1H), 2.99 (s, 3H), 2.85-2.73 (m, 1H), 2.67-2.55 (m, 1H), 2.44-2.32 (m, 2H), 2.03-1.91 (m, 1H), 1.72-1.61 (m, 1H), 0.99-0.83 (m, 2H), 0.70-0.60 (q, 6H), 0.60-0.45 (m, 1H); MS (ESI) m/z 696 (M+H+).

Provenance & Evidence