1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 117703055, compound

Participants

Reaction Steps

To a solution in which the 4-((3,4,5-tris(2-(2-((4-(((3-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromen-7-yl)(isopropyl)amino)methyl)-1H-1,2,3-triazol-1-yl)methoxy)ethoxy) ethoxy)benzamido)methyl)benzoic acid (100 mg, 0.053 mmol) compound of Chemical Formula 17 was dissolved in methylene chloride (2 mL), N-hydroxy succinimide (243.9 mg, 2.12 mmol) and EDAC (406.4 mg, 2.12 mmol) were added in order at 0° C., and the mixture was stirred overnight at room temperature. After the post-reaction mixture was partitioned to methylene chloride (20 mL) and distilled water (20 mL), the separated organic layer was washed with saturated salted water (10 mL), dried with anhydrous sodium sulfate, then filtered, and the resulting filtrate was vacuum distilled. The residue obtained was column chromatographed on silica gel (chloroform/methanol (20:1)) to give 2,5-dioxopyrrolidin-1-yl 4-((3,4,5-tris(2-(2-((4-(((3-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromen-7-yl)(isopropyl)amino)methyl)-1H-1,2,3-triazol-1-yl)methoxy)ethoxy)ethoxy)benz amido)methyl)benzoate (96 mg, 92%). 1H NMR (500 MHz, CDCl3) δ 10.04 (s, 3H), 8.32 (d, 2H, J=8.2 Hz), 8.11 (d, 3H, J=9.6 Hz), 7.93 (d, 4H, J=7.3 Hz), 7.74 (d, 3H, J=7.3 Hz), 7.45-7.60 (m, 9H), 7.37 (m, 3H), 6.82 (m, 3H), 6.65 (s, 3H), 4.53-4.70 (m, 14H), 4.34 (m, 3H), 4.01-4.13 (m, 6H), 3.82 (m, 9H), 3.65 (m, 6H), 3.52 (m, 12H), 2.91 (s, 4H), 1.25 (d, 18H, J=6.4 Hz).

Provenance & Evidence