1,2-Dichloroethane → HCID 11224578, compound

Participants

Reaction Steps

To a mixture of EDC (0.08 g, 0.42 mmol), HOBT (0.056 g, 0.42 mmol) and (S)-2-(3-biphenyl-4-yl-ureido)-3-phenyl-propionic acid (Example 13, step A)(0.1 g, 0.28 mmol) in DMF (3 mL), N′-isopropyl-ethane-1,2-diamine (0.054 g, 0.42 mmol) was added at rt followed by N-methyl morpholine (0.056 g, 0.55 mmol). The solution was stirred for 6 h, diluted with EtOAc (100 mL), washed with saturated NaHCO3 (2×20 mL) and brine (2×20 mL), and dried (Na2SO4). The solvent was removed, and the residue was purified by flash column chromatography using 0–20% MeOH (1% NH4OH)/CH2Cl2 to afford 0.07 g (57%) of the desired product. MS (electrospray): mass calculated for C27H32N4O2, 444.25; m/z found, 445.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.89 (s, 1H), 8.18 (t, J=5 Hz, 1H), 7.61–7.2 (m, 14H), 6.53 (d, J=8 Hz, 1H), 4.46 (m, 1H), 3.16 (m, 2H), 2.9 (dd, J=13.7, 5.8 Hz, 1H), 2.86 (dd, J=13.7, 7.72 Hz, 1H), 2.79 (m, 1H), 2.58 (m, 2H), 0.98 (d, J=6.2 Hz, 6H).

Provenance & Evidence