1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59704208, compound

Participants

Reaction Steps

To an oven-dried carousel reaction flask charged with a magnetic stir bar at room temperature under argon was added (R)-2,7,8-triamino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene (0.200 g, 0.479 mmol), Fmoc-Ala-OH (0.179 g, 0.575 mmol), dimethylformamide (2.4 mL), HOBt 0.084 g, 0.62 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) (0.119 g, 0.623 mmol). The black solution was stirred at room temperature overnight. The solution was diluted with EtOAc (50 mL), washed with water (3×30 mL), brine (10 mL), dried over MgSO4, filtered and concentrated to give the crude product as a brown residue. Purification by flash column chromatography (silica gel 12 g pre-packed column, gradient elution with EtOAc:Hexanes, 1:9 to 1:4 to 1:1) gave 0.046 g (13%) of the title compound as a yellow solid: mp: 212-217° C. (dec); 1H-NMR (DMSO-d6): δ 9.37 (br s, 1H), 7.89 (d, J=7.7 Hz, 2H), 7.76-7.69 (m, 3H), 7.44-7.39 (m, 2H), 7.35-7.30 (m, 2H), 6.98 (d, J=1.9 Hz, 1H), 6.88 (br s, 2H), 6.88 (d, J=8.0 Hz, 1H), 6.86 (d, J=1.9 Hz, 1H), 6.31 (d, J=8.3 Hz, 1H), 4.79 (br s, 2H), 4.69 (s, 1H), 4.31-4.23 (m, 4H), 3.80 (s, 3H), 3.70 (s, 3H), 1.32 (d, J=6.9 Hz, 3H).

Provenance & Evidence