Cyclopropylamine → (S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tertbutyl ester

Participants

Reaction Steps

A mixture of (S)-2-[4-(4-carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.51 g, 1.22 mmol), HATU (0.47 g, 1.24 mmol)), and DIEA (0.2 mL, mmol) in DMF (10.0 mL) was stirred at room temperature for 1 h. Cyclopropyl amine (0.2 mL, 1.53 mmol) was added and the reaction mixture was stirred at room temperature overnight. The resulting mixture was purified by reverse phase HPLC to furnish the desired product. 1HNMR (DMSO-d6) δ(ppm) 12.45-12.40 (m, 1H), 8.44-8.43 (d, 1H), 7.95-7.2 (m, 5H), 4.43-4.34 (m, 1H), 2.97-2.82 (m, 2H), 2.26-2.19 (m, 1H), 1.94-1.79 (m, 3H), 1.39-1.24 (m, 9H), 0.73-0.55 (m, 4H); MS: 457.2 (M+H+).

Provenance & Evidence