Triethylamine → HCID 24877035, compound

Participants

Reaction Steps

(2S)N-[1-(2-Amino-4-methylpentanoyl)-piperidin-3-yl]-N-cyclo-propyl-3-trifluoromethylbenzenesulfonamide (8) was prepared as follows. A solution of compound 6 (see Example 1) (300 mg, 0.78 mmol), triethylamine (TEA, 0.5 mL), 1-hydroxybenzotriazole (HOBT) (100 mg), compound 2 (0.2 g, 0.86 mmol, Adv. Chem. Tech.), and dichloromethane (DCM, 4 mL) was cooled with ice-water and treated with diisopropyl azodicarboxylate (DIC) (0.14 mL, 0.88 mmol). The resulting mixture was warmed to room temperature over 24 hours. The reaction mixture was cooled to 0° C. and the solid was removed by filtration. The liquid was concentrated and purified by column (silica) eluting with EtOAc/hexanes (1/1) to afford the BOC-protected product, which was dissolved in 1,4-dioxane (4 mL) and treated with HCl (4N in 1,4-dioxane 1 mL) at room temperature for 4 hours. The solvent was removed under vacuum and the residue was washed with Et2O (3×2 mL) to give the title compound 8 as a HCl-salt (white solid, 300 mg, yield 79%). 1H NMR (400 MHz, CD3OD): δ 7.90-8.28 (m, 4H, Ar—H), 4.15-4.55 (m, 2H), 3.75-3.95 (m, 2H), 3.35-3.45 (m, 0.5H), 3.05-3.15 (m, 0.5H), 2.85-2.95 (m, 0.5H), 2.55-2.65 (m, 0.5H), 1.45-2.15 (m, 8H), 0.75-1.15 (m, 10H). LC: 100%; MS: m/z=462 (M+1).

Provenance & Evidence