Diisopropylethylamine → HCID 87499345, compound

Participants

Reaction Steps

2-[4-(2-Carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (IS2277-52, 125 mg, 0.28 mmol) was dissolved in 4 mL of DMF. To this solution was added HATU (160.9 mg, 0.42 mmol) and DIEA (0.05 mL, 0.36 mmol). This solution was stirred at room temperature for 1 hour. To this solution was added 48.2 mg (0.28 mmol) of 3-amino-azetidine-1-carboxylic acid tert-butyl ester. Reaction mixture was stirred at room temperature overnight to yield crude 2-{4-[4-(1-tert-butoxycarbonyl-azetidin-3-ylcarbamoyl)-phenyl]-thiazol-2-ylcarbamoyl}-pyrrolodine-1-carboxylic acid benzyl ester, which was then purified using reverse phase HPLC. The purified material was dissolved in 4 mL of 1:1 solution of CH2Cl2/TFA and stirred for 1.5 hours at room temperature. Reaction mixture was evaporated under reduced pressure to give pure desired product. MS: 506.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 12.50 (br s, 1H), 8.47 (br s, 1H), 7.91 (m, 5H), 7.10 (m, 4H), 5.31 (br s, 1H), 5.02 (m, 2H), 4.51 (m, 1H), 4.08 (m, 3H), 2.47 (m, 3H), 2.23 (m, 1H), 1.90 (m, 4H), 1.94 (m, 2H).

Provenance & Evidence