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 (200 mg, 0.49 mmol) in CH2Cl2 (10 mL) was added HOBt (100 mg, 0.69 mmol) and EDCI (140 mg, 0.69 mmol). The mixture was stirred for 1 h and O-(2-(vinyl-oxy)ethyl)hydroxylamine (72 mg, 0.69 mmol) was added. After stirring for 4 h at ambient temperature, the reaction was treated with saturated NH4Cl (aq.). The resultant mixture was extracted with CH2Cl2 (15 mL×3). The combined organic extracts were washed with water (10 mL) 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, 50:1, v/v) and gave the desired product (yellow solid, 190 mg, 79.7% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.85 (s, 1H), 8.65 (s, 1H), 8.51 (s, 1H), 7.38 (d, 1H), 7.29 (d, 1H), 6.64 (dd, 1H), 6.42 (d, 1H), 4.21 (d, 1H), 4.01 (m, 3H), 3.83 (m, 2H).

Provenance & Evidence