Hydrochloric Acid → Ammonium Acetate

Participants

Reaction Steps

A mixture of Example 42b (160 mg, 0.356 mmol), cyclohexane-1,2-diamine (81 mg, 0.713 mmol), triethylamine (0.10 ml, 0.713 mmol) and dioxane (4 ml) was heated at 60° C. for 2 hours. The reaction mixture was concentrated in vacuo. To a mixture of the residue in methanol (10 mL) was added dropwise NaOH solution (1.43 ml, 1.43 mmol). The mixture was stirred at room temperature for 40 minutes. The reaction mixture was neutralized with dilute hydrochloric acid and purified by reverse-phase HPLC performed on a Phenomenex Luna C8 AXIA column (30×75 mm, 100 Å) using a gradient of 10% to 95% acetonitrile: 10 mM ammonium acetate in water over 12 minutes at a flow rate of 50 mL/minutes to give the title compound. MS (ESI) m/e 343 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 1.13-1.43 (m, 4H) 1.55-1.77 (m, 4H) 2.03-2.14 (m, 1H) 2.62-2.71 (m, 1H) 6.98-7.06 (m, 1H) 7.06-7.11 (m, 1H) 7.15-7.21 (m, 1H) 8.28 (dd, J=4.73, 1.68 Hz, 1H) 8.32-8.37 (m, 1H) 8.74-8.85 (m, 1H).

Provenance & Evidence