1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 89705069, compound

Participants

Reaction Steps

To a solution of 4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d][1,2,3]thiadiazole-6-carboxylic acid (1.7 g, 5.54 mmol) in CH2Cl2 (20 mL) was added HOBt (1.21 g, 8.31 mmol) and EDCI (1.59 mg, 8.31 mmol). The mixture was stirred for 1 h and O-(2-(vinyl-oxy)ethyl)hydroxylamine (0.69 g, 6.65 mmol) was added. After stirring for 4 h at ambient temperature, the reaction was treated with saturated NH4Cl (aq., 20 mL). The resultant mixture was extracted with CH2Cl2 (15 mL×3). The combined organic extracts were washed with water (10 mL×3) and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 20:1, v/v) and gave the desired product (2.44 g, 85% yield). 1H NMR (400 MHz, d6-DMSO) δ 11.85 (s, 1H), 8.65 (s, 1H), 8.51 (s, 1H), 7.38 (d, J=10.8 Hz, 1H), 7.29 (d, J=8.1 Hz, 1H), 6.64 (dd, J=13.9, 6.6 Hz, 1H), 6.42 (d, J=6.0 Hz, 1H), 4.21 (d, J=14.5 Hz, 1H), 4.01 (m, 3H), 3.83 (m, 2H).

Provenance & Evidence