Water → HCID 69654978, compound

Participants

Reaction Steps

To a stirred mixture of pyridine-3-sulfonic acid-[4-(4-oxo piperidine-1-yl)-phenyl]amide (which was obtained in Example 237) (0.94 g, 2.8 mmol), N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) (0.70 g, 2.8 mmol) in dimethylformamide (10 mL) at room temperature was added sodium triacetoxyborohydride (0.72 g, 3.4 mmol) and glacial acid (0.18 mL, 3.1 mmol). The reaction was stirred under N2 atmosphere for 18 hours. The reaction mixture was poured onto 1:1 water/saturated sodium bicarbonate, extracted with ethyl acetate three times, dried over sodium sulfate and concentrated. The product was purified by flash silica gel chromatography eluting with 10% methanol in methylene chloride and finally with 20% methanol in methylene chloride to give the titled compound as a yellow solid (0.23 g, 15%); 1H NMR (300 MHz, DMSO-d6) δ 1.25-1.45 (m, 2H), 1.80-1.95 (m, 2H), 2.50-2.80 (m, 5H), 2.92 (s, 3H), 3.40-3.55 (m, 2H), 4.45-4.60 (m, 1H), 6.85-6.90 (m, 5H), 7.02 (dd, J=8.3, 2.0 Hz, 1H), 7.18 (d, J=2.0 Hz, 1H), 7.59 (dd, J=7.4, 4.4 Hz, 1H), 7.95-8.05 (m, 2H), 8.70-8.80 (m, 2H); MS (ES) m/z: 561.95 (MH+, 100%); HRMS Calcd. for C25H32N5O6S2 (MH+): 562.1788. Found: 562.1774.

Provenance & Evidence