Pyrrolidine → HCID 68983650, compound

Participants

Reaction Steps

N-Cyclopropyl-N-[1-(3-pyrrolidin-1-ylhexanoyl)piperidin-4-yl]-3-trifluoromethylbenzenesulfonamide (43) was prepared by reacting N-cyclopropyl-N-(1-hex-2-enoyl-piperidin-4-yl)-3-trifluoromethyl-benzenesulfonamide (30) (250 mg, 0.56 mmol) and pyrrolidine (2 mL) as described in Example 26 above. The residue was chromatographed over flash silica eluting with ethyl acetate:methanol:ammonia (100:10:1) to give the title compound 43 as a white solid (140 mg, 48%). LC: 98.9%. m/z=516.3, 517.3 (M+H). 1H NMR (400 MHz, CDCl3): (1:1 mixture of rotamers) δ 8.14 (1H, s), 8.05 (1H, d, J=7.5 Hz), 7.86 (1H, d, J=7.5 Hz), 7.70 (1H, t, J=7.5 Hz), 4.75 (1H, d, J=15 Hz), 4.10 (1H, m), 3.97 (1H, d, J=15 Hz), 3.05 (2H, m), 2.65-2.45 (6H, m), 2.35 (1H, m), 1.96 (1H, m), 1.85-1.30 (16H, m), 0.98 (1H, m), 0.92-0.70 (6H, m).

Provenance & Evidence