1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67376539, compound

Participants

Reaction Steps

To a solution of the product of Example 58D (225 mg, 0.679 mmol) and the product of Example 165A (135 mg, 0.679 mmol) in 1,4-dioxane (4 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.120 mL, 0.679 mmol) via syringe. The reaction was stirred at ambient temperature for 2.5 hours, then heated to 60° C. for 44 hours. The reaction was cooled to ambient temperature, diluted with ethyl acetate, and washed with 3 N aqueous HCl resulting in a homogeneous solution. Brine was added to force the phase separation. The organic layer was separated and washed with saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50% ethyl acetate/hexanes) yielded the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.36-7.27 (m, 4H), 7.27-7.21 (m, 2H), 7.15-7.07 (m, 2H), 7.07-6.96 (m, 4H), 4.79 (s, 2H), 3.46 (t, J=6.4, 2H), 3.00 (s, 4H), 2.80 (t, J=6.4, 2H); MS (ESI+) m/z 511 (M+NH4)+.

Provenance & Evidence