Triethylamine → HCID 69654936, compound

Participants

Reaction Steps

A mixture of 4-methoxy-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 218) (0.288 g, 0.8 mmol) and (1R)-2-amino-1-(3-chloro-phenyl)-ethanol hydrochloride (which was obtained in Example 1) (0.832 g, 4.0 mmol) was dissolved in 50 mL of methanol and the pH was adjusted to 5 with triethylamine. After stirred at room temperature for one day acetic acid (1 mL) and NaCNBH3 (50 mg, 0.8 mmol) were then added. The reaction was stirred for another day, the solvent was removed, and the residue was purified by thin layer chromatography (10% methanol/CH2Cl2) to give the title compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40–1.60 (m, 2 H), 1.95–2.10 (m, 2 H), 2.50–3.10 (m, 5 H), 3.50–3.70 (m, 2 H), 3.79 (s, 3 H), 4.80–4.90 (m, 1 H), 6.79 (d, J=9.0 Hz, 2 ) 6.89 (d, J=9.0 Hz, 2 H), 7.05 (d, J=9.0 Hz, 2 H), 7.30–7.50 (m, 4 H), 7.60 (d, J=9.0 Hz, 2 H), 9.60 (brs, 1 H); MS (ES) m/z: 516.2 (MH+); HRMS Calcd. for C26H31ClN3O4S (MH+); 516.1724. Found: 516.1713.

Provenance & Evidence