Diisopropylethylamine → HCID 44609944, compound

Participants

Reaction Steps

To a 50 mL vial charged with a magnetic stir bar was added (S,Z)-5-(2-(3-aminopyrrolidin-1-yl)-3-chlorobenzylidene)thiazolidine-2,4-dione (75 mg, 0.23 mmol) (Example 86), 1-methyl-1H-imidazole-2-carboxylic acid (87 mg, 0.69 mmol), HATU (220 mg, 0.58 mmol) and dichloromethane (5 mL). Hunig's base (0.202 mL, 1.16 mmol) was then added and the mixture was stirred at rt for 4 h. The reaction was then diluted with dichloromethane and washed with water. The mixture was separated with a phase separator tube and the organic phase was evaporated to dryness. The residue was purified by reverse phase chromatography to afford the title compound as a yellow solid (21 mg, 21%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (s, 1 H) 7.51 (dd, 1 H) 7.41 (dd, 1 H) 7.18-7.27 (m, 2 H) 7.01 (s, 1 H) 4.67-4.77 (m, 1 H) 4.00 (s, 3 H) 3.63-3.75 (m, 2 H) 3.47-3.54 (m, 1 H) 3.36-3.47 (m, 1 H) 2.39-2.51 (m, 1 H) 2.14 (dd, 1 H); m/z 432.

Provenance & Evidence