1,2-Dichloroethane → HCID 54698990, compound

Participants

Reaction Steps

To a solution of 5-fluoro-2-[({[(7S)-3-hydroxy-5-methyl-4-oxo-7-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl]carbonyl}amino)methyl]benzoic acid (47 mg, 0.106 mmol) in DMF (1 mL) were added HOAT (44 mg, 0.322 mmol), and EDC (62 mg, 0.322 mmol). The reaction mixture was stirred at ambient temperature 15 minutes then 2M methylamine in THF (214 μL, 0.429 mmol) and triethylamine (45 μL, 0.322 mmol) were added. The reaction was stirred at ambient temperature for 5 hours. The crude reaction was purified by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA). Collection and concentration of the appropriate fractions afforded the product as a light pink solid. 1H NMR (400 MHz, d6-DMSO) δ 8.55 (t, J=6.2 Hz, 1H), 8.48 (m, 1H), 7.3-7.4 (m, 4H), 7.25 (m, 2H), 7.03 (m, 2H), 5.75 (t, J=4.0 Hz, 1H), 4.68 (ABX, J=15.2, 6.4 Hz, 2H), 4.18 (dd, J=13.4, 4.6 Hz, 1H), 3.79 (dd, J=13.4, 3.8 Hz, 1H), 2.87 (s, 3H), 2.75 (d, J=4.6 Hz, 3H); HRMS (FT-ICR) C23H22FN5O4+H=452.1735; calculated 452.1729.

Provenance & Evidence