1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58094808, compound

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Reaction Steps

A mixture of 5-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-3-phenylthiophene-2-carboxylic acid (100 mg, 0.299 mmol), EDCI (450 mg, 2.35 mmol), HOBt (95 mg, 0.703 mmol), triethylamine (2.5 mL), ammonium chloride (870 mg, 16.3 mmol) and DMF (35 mL) was stirred for 16 h at rt. To the mixture, were added water and EtOAc and the resulting biphasic mixture was vigorously stirred for 30 min. The organic phase was washed with water and brine and then dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was washed with EtOAc and diisopropyl ether to yield the title compound (72 mg, 71%) as a pale yellow solid. 1H NMR (300 MHz, d6-DMSO) δ: 8.68 (d, J=7.0 Hz, 1H), 7.92 (d, J=9.1 Hz, 1H), 7.70-7.53 (m, 2H), 7.53-7.31 (m, 4H), 7.26 (s, 1H), 7.11-6.71 (m, 3H), 2.59 (s, 3H).

Provenance & Evidence