1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58921037, compound

Participants

Reaction Steps

To a solution of (1S,2R)-2-(3-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)ureido)cyclohexanecarboxylic acid (11.6 mg, 0.019 mmol) and methyl 4-aminobutanoate (3.2 mg, 0.027 mmol) in CH2Cl2 (185 μL), was added EDCI (4.6 mg, 0.024 mmol) followed by DMAP (2.9 mg, 0.024 mmol) at room temperature. The reaction mixture was stirred at room temperature until starting material was consumed as indicated by HPLC analysis. The reaction mixture was concentrated to dryness and the resulting residue was taken up in MeOH and purified by preparative HPLC (Phenoma Luna AXIA 10A, C18; mobile phase: MeCN/H2O/TFA) to provide methyl 4-((1S,2R)-2-(3-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)ureido)cyclohexanecarboxamido)butanoate as white solid (7.1 mg, 53% yield). LC/MS RT=3.200 min; [M+H] 711.1 (LCMS Method 4), NMR: 500 MHz 1H (CDCl3) 8.19 ppm, 1 H, d, J=2.20 Hz; 7.57 ppm, 1 H, dd, J=8.25, 2.20 Hz; 7.04 ppm, 6 H, m; 6.99 ppm, 2 H, t, J=7.42 Hz; 6.79 ppm, 1 H, d, J=8.25 Hz; 6.52 ppm, 2 H, d, J=7.15 Hz; 6.18 ppm, 1 H, s; 5.78 ppm, 1 H, m; 4.28 ppm, 1 H, d, J=12.65 Hz; 3.87 ppm, 1 H, s; 3.61 ppm, 3 H, m; 3.47 ppm, 2 H, m; 3.40 ppm, 1 H, m; 2.40 ppm, 5 H, m; 1.58 ppm, 9 H, m.

Provenance & Evidence