1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178448506, compound

Participants

Reaction Steps

A mixture of the compound from Example 2A (1.2 g, 6.4 mmol), 5-chloro-2-methoxy-benzoic acid (1.4 g, 7.7 mmol), EDCI (2.45 g, 12.8 mmol), HOBt (1.7 g, 12.8 mmol) and DMAP (78 mg, 0.64 mmol) in pyridine (40 mL) was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, diluted with water, and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, eluting with ethyl acetate/hexanes 1:3) to provide 919 mg of title compound. MS (APCI) m/z 355 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.4 Hz, 3H) 1.31 (m, 2H) 1.45 (s, 6H) 1.60 (m, 2H) 3.53 (m, 2H) 3.63 (t, J=7.4 Hz, 2H) 3.77 (s, 3H) 7.09 (d, J=8.9 Hz, 1H) 7.45 (dd, J=8.9, 2.8 Hz, 1H) 7.64 (d, J=2.8 Hz, 1H).

Provenance & Evidence