Diisopropylethylamine → HCID 178502358, compound

Participants

Reaction Steps

To a solution of (S)-4-(4′-bromo-[1,1′-biphenyl]-4-yl)-2-(pyrrolidin-2-yl)-1H-imidazole hydrochloride (423 mg, 1.045 mmol) in DMF (5 mL) is sequentially added (2S)-2-(methoxycarbonylamino)-3-methyl-butanoic acid (201.5 mg, 1.150 mmol), DIPEA (405.2 mg, 546.1 μL, 3.135 mmol) and HATU (596.2 mg, 1.568 mmol) under nitrogen atmosphere. The reaction mixture is stirred at room temperature for 2 hours and diluted with saturated aqueous NaHCO3 (10 mL). The reaction mixture is extracted with EtOAc (5×10 mL), and the combined organic layer are washed with H2O (3×10 mL), and concentrated to dryness. The residue is purified by flash column chromatography on silica gel (2 to 20% methanol in CH2Cl2) to give methyl ((S)-1-((S)-2-(4-(4′-bromo-[1,1′-biphenyl]-4-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate (462 mg, 84%).

Provenance & Evidence