Triethylamine → HCID 178427911, compound

Participants

Reaction Steps

To a solution of Example 34 (200 mg, 0.48 mmol) in dichloromethane (15 mL) was added triethyloxonium tetrafluoroborate (0.96 mL, 0.96 mmol, 1 Min dichloromethane) and the mixture was stirred at room temperature for overnight. The reaction mixture was then heated to 50° C. for 3 more days with continued stirring. The reaction mixture was cooled, concentrated and triturated in ether. The obtained product was dissolved in ethanol (2 mL) and cyanamide (61 mg, 1.4 mmol) and triethylamine (0.2 mL, 1.4 mmol) were added. After stirring, at 80° C. for 16 hours, the reaction mixture was cooled, diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash 280™ (SiO2, 0-100% of ethyl acetate in hexanes). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04-1.34 (m, 5H), 1.44-1.91 (m, 9H), 2.60 (s, 3H), 2.60-2.70 (m, 1H), 2.83-2.98 (m, 1H), 3.08 (t, J=11.4 Hz, 1H), 3.64 (t, 3H), 7.47 (t, J=8.3 Hz, 1H), 7.80 (dd, J=8.1, 1.0 Hz, 1H), 7.83-7.89 (m, 1H), 8.31 (d, J=7.5 Hz, 1H); MS (ESI+) m/z 423 (M+H)+. Anal. Calculated for C20H27ClN4O2S: C, 56.79; H, 6.43; N, 13.29. Found: C, 56.42; H, 6.41; N, 12.98.

Provenance & Evidence