Ethanolamine → methyl 3-chloro-4-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

To a solution of 4-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid (0.075 g, 0.368 mmol) in DMF (1 ml) was added DIPEA (0.097 ml, 0.553 mmol), HATU (0.168 g, 0.442 mmol) and ethanolamine (0.033 ml, 0.553 mmol) and the reaction stirred at RT for 3 h. Purification was accomplished by HPLC to afford methyl 3-chloro-4-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate (0.06 g, 53% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (br. s., 1H) 7.78 (t, 1H) 7.52 (d, 1H) 4.28 (br. s., 1H) 3.80 (s, 3H) 3.56-3.68 (m, 1H) 3.46 (t, 1H) 3.25 (q, 1H) 3.07-3.21 (m, 1H). MS: m/z 247.0 (M+1).

Provenance & Evidence