Triethylamine → HCID 178490003, compound

Participants

Reaction Steps

A solution of N-(3-aminopropyl)-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorobenzenesulfonamide (172 mg, 0.27 mmol), N,N′-di-Boc-1H-pyrazole-1-carboxamidine (100 mg, 0.32 mmol) and Et3N (190 μL, 1.35 mmol) in MeOH (10 mL) was stirred at 25° C. for 18 h. The reaction mixture was concentrated and reconstituted in EtOAc. The organic layer was washed with 1N HCl (3×5 mL), satd NaHCO3 (5 mL), dried over Na2SO4 and concentrated to a colorless oil. To the oil was added 4N HCl in dioxane (10 mL) at 25° C. and stirred for 18 h. Upon completion, the reaction mixture was concentrated and purified by preparatory HPLC (MeCN/H2O with 0.1% TFA, 10-99%) to give the title product (54 mg, 28% yield) as white solid. 1H NMR (400 MHz, MeOD) δ 7.99 (s, 1H), 7.51 (s, 2H), 7.37 (s, 1H), 7.28 (d, J=5.7 Hz, 1H), 6.98 (s, 2H), 6.62 (s, 2H), 6.56 (s, 2H), 4.14 (s, 2H), 3.73 (s, 3H), 3.70-3.54 (m, 3H), 3.30-3.21 (m, 2H), 3.00 (s, 2H), 1.80 (s, 2H), 1.63 (s, 6H); MS (EI) m/z 681 (MH+).

Provenance & Evidence