1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 45274931, compound

Participants

Reaction Steps

N1-((Ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.132 mL, 0.743 mmol) was added via syringe to a mixture of the product of Example 68E (230 mg, 0.743 mmol), 1-(piperidin-4-yl)-5-(trifluoromethyl)-1H-benzo[d][1,2,3]triazole (201 mg, 0.743 mmol), and 4-(dimethylamino)pyridine (9.1 mg, 0.07 mmol) in CH2Cl2 (3 mL). The reaction was allowed to proceed at ambient temperature for 23 hours. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with 1 N aqueous HCl, saturated aqueous NaHCO3 solution and brine, dried with Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50%-100% ethyl acetate/hexanes, 0-20 minutes, 30 mL/minute) to yield an amorphous solid which was triturated with 12 mL 1:1 ether/hexanes and 2 mL ether. The solid was collected by vacuum filtration and air-dried to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.37 (s, 1H), 7.73 (d, J=8.7, 1H), 7.51 (d, J=8.4, 1H), 7.39-7.14 (m, 10H), 5.10-4.95 (m, 1H), 4.82-4.66 (m, 1H), 4.34 (d, J=15.1, 1H), 4.27-4.06 (m, 2H), 3.71-3.50 (m, 2H), 3.46-3.29 (m, 1H), 3.14-2.94 (m, 1H), 2.73-2.63 (m, 2H), 2.64-2.47 (m, 1H), 2.44-2.14 (m, 3H), 1.96-1.82 (m, 2H). MS (ESI+) m/z 562 (M+H)+.

Provenance & Evidence