1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 76852798, compound

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Reaction Steps

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18, 88 mg, 0.403 mmol) and 2-phenyl-1-(S)-(2-phenyl-[1,3]dioxolan-2-yl)ethylamine (Preparation 95, 104 mg, 0.386 mmol) in DMF (5 mL) was added HOBt (65 mg, 0.424 mmol), DIPEA (0.155 mL, 0.890 mmol) and EDCI (90 mg, 0.469 mmol). After stirring at rt for 12 h the mixture was added to diluted brine (100 mL, water/brine: 1/1). Extraction with ethyl acetate (4×25 mL), washing of the combined extracts with diluted hydrochloric acid (1M, 30 ml), diluted aqueous sodium hydroxide solution (1M, 30 ml) and brine (50 mL) followed by drying (MgSO4) gave after concentration a residue which was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate: 50/50). The title compound was obtained as a colourless oil. δH (CDCl3): 2.73 (1H, dd), 3.10 (1H, dd), 3.84-4.22 (4H, 4m), 5.01 (1H, ddd), 6.37 (1H, d), 6.72 (1H, s), 7.05-7.62 (11H, 3m), 8.64 (1H, s), 10.48 (1H, s); m/z (ES+)=448.24 [M+H]+; RT=3.64 min.

Provenance & Evidence