Diisopropylethylamine → HCID 58118621, compound

Participants

Reaction Steps

To a solution of N-[4-((R)-1-Aminoethyl)-5-fluoro-2-methylphenyl]methanesulfonamide hydrochloride (25 mg, 0.09 mmol), 6-trifluoromethyl-2,3-dihydro[1,4]dioxino[2,3-b]pyridine-2-carboxylic acid (20 mg, 0.08 mmol), 4-dimethylaminopyridine (0.8 mg, 0.8 mop and N,N-diisopropylethylamine (50 μL, 0.29 mmol) in anhydrous DMF (1 mL) was added HATU (34 mg, 0.09 mmol). The reaction was stirred overnight at room temperature, then poured into saturated NaHCO3 solution (20 mL) and extracted with EtOAc (3×20 mL). The combined organics were washed with brine (3×30 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 3.5% MeOH in DCM) gave the title compound (24 mg, 60%) as a solid. m/z=478.2 (M+1), r.t.=2.98 mins. 1H NMR (400 MHz; DMSO-d6) 9.20 (1H, dd), 8.82 (1H, dd), 7.51-7.43 (2H, m), 7.27 (0.5H, d), 7.14 (0.5H, d), 7.07 (1H, dd), 5.20-5.17 (1H, m), 5.09 (1H, t), 4.48-4.42 (2H, m), 3.01 (3H, d), 2.27 (1.5H, s), 2.21 (1.5H, s), 1.38 (3H, d).

Provenance & Evidence