1,2-Dichloroethane → HCID 24877156, compound

Participants

Reaction Steps

(2S)N-Cyclopropyl-N-[1-(2-isopropylamino-4-methylpentanoyl)-piperidin-3-yl]-3-trifluoromethylbenzenesulfonamide (18) was prepared as follows. A solution of compound 8 prepared in Example 2 (100 mg, 0.22 mmol), compound 17 (12 mg, 0.22 mmol, Aldrich) and 4 Å molecular sieves (500 mg) in 2 mL of 1,2-dichloroethane was shaken at room temperature for 10 minutes, and then, NaB(OAc)3H (43 mg, 0.22 mmol) was charged. The resulting mixture was shaken at room temperature for 24 hours. The reaction mixture was quenched with MeOH (0.2 mL), water (2 mL) was added, and the mixture was extracted with DCM (3×4 mL). The organic layers were combined and then washed with brine, dried over Na2SO3, concentrated under vacuum and purified by column (silica gel, EtOAc, then EtOAc/MeOH 10/1) to give the title compound 18 as a free base, which was converted to its HCl-salt by treating with HCl (1 N aqueous) and drying under vacuum (white solid, 60 mg, yield 65%). 1H NMR (400 MHz, CD3OD): δ 8.10-8.22 (m, 2H), 8.06 (dd, j=7.7, 7.8 Hz, 1H), 7.91 (dd, j=7.8, 7.9 Hz, 1H), 4.45-4.55 (m, 2H), 3.75-3.95 (m, 2H), 3.35-3.45 (m, 1H), 3.3-3.35 (m, 1H), 2.9-2.95 (m, 0.5H), 2.55-2.64 (m, 0.5H), 1.35-2.15 (m, 14H), 0.75-1.20 (m, 10H); LC: 100%; MS: m/z=504 (M+1).

Provenance & Evidence