Dimethylformamide → HCID 57526938, compound

Participants

Reaction Steps

A 50-mL RB-flask was charged with 4-{[(5-acetyl-6-(3,4-difluorophenyl)-4-methyl-2-oxo-3,6-dihydro-1(2H)-pyrimidinyl)carbonyl]amino}butanoic acid (313 mg, 0.854 mmol), tert-butyl-4-[3-(amino)phenyl]-1-piperidinecarboxylate (235 mg, 0.857 mmol), 1-[3-(Dimethylamino)propyl]-3-ethylcarbodimide hydrochloride (7.71 mmol, 265 mg), 4-dimethylaminopyridine (10.4 mg, 0.0854 mmol) in DMF:DCM (0.8:8.0 mL) at room temperature. The reaction mixture was stirred for 12 h and water (20.0 mL) was added to the reaction mixture. The organic layer was separated and the aqueous layer was extracted with CHCl3 (3×10 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed (silica, hexanes:EtOAc 9:1) to afford the desired product (378 mg, 67.8%): 1H NMR (400 MHz, CDCl3) δ 8.03 (m, 2H), 7.57 (s, 1H), 7.36-7.28 (m, 3H), 7.27-7.22 (m, 1H), 6.97-6.89 (m, 3H), 6.72 (s, 1H), 3.72 (s, 3H), 3.47-3.37 (m, 2H), 2.42 (s, 3H), 2.37-2.29 (m, 2H), 1.98-1.91 (m, 2H), 1.86-1.75 (m, 2H), 1.72-1.54 (m, 7H), 1.48 (s, 9H); ESMS m/e: 554.3 (M−100).

Provenance & Evidence