1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178426293, compound

Participants

Reaction Steps

To a solution of COMPOUND 249 (93 mg, 0.30 mmol) in dry DMF (3 mL) was added imidazole-4-carboxylic acid (50 mg, 0.45 mmol) followed by EDCI (84 mg, 0.44 mmol), and DMAP (112 mg, 0.92 mmol). The mixture was stirred at room temperature overnight. The mixture was diluted with water (10 mL) and brine (10 mL) and extracted with CH2Cl2 (5×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2-MeOH—NH4OH) provided 36 mg (30%) of COMPOUND 273 as a white solid. 1H NMR (CDCl3) δ 1.60-1.76 (m, 4H), 1.95-2.09 (m, 8H), 2.60-3.02 (m, 3H), 3.83 (br s, 3H), 4.73 (br s, 1H), 7.09 (dd, 2H, J=7.2, 4.8 Hz), 7.36-7.54 (m, 3H), 7.65 (br s, 1H), 8.34 (d, 2H, J=4.2 Hz); ES-MS m/z 405 (M+H).

Provenance & Evidence