Pyridine → HCID 66717083, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL screw cap vial equipped with a magnetic stir bar was added triphosgene (20 mg, 0.068 mmol) in toluene (0.85 mL). The mixture was cooled to 0° C. and pyridine (0.017 mL, 0.21 mmol) was added followed by 188 (38 mg, 0.17 mmol) in toluene (0.5 mL). The reaction was stirred at 0° C. for 1 h then room temperature overnight. The reaction was concentrated in vacuo then taken up in DCM (1.0 mL) and cooled to 0° C. Methylamine HCl (57 mg, 0.85 mmol) was added followed by triethylamine (0.237 mL, 1.7 mmol). The reaction was allowed to warm to room temperature and was stirred for 18 h. The reaction was concentrated in vacuo and the residue was purified by preparative HPLC-MS using 20-45% MeCN in water as the gradient. The appropriate fractions were collected and concentrated in vacuo to give the title compound as a white solid (14 mg, 29% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (d, J=6.82 Hz, 3H) 1.72-1.83 (m, 2H) 2.51-2.55 (m, 2 H) 2.56 (d, J=4.80 Hz, 3H) 3.92 (t, J=6.57 Hz, 2H) 4.57-4.64 (m, 1H) 6.69 (d, J=1.77 Hz, 1 H) 6.74 (dd, J=8.08, 2.02 Hz, 1H) 6.86 (d, J=8.08 Hz, 1H) 6.94-7.03 (m, 1H) 10.60 (s, 1H). ESI-MS: m/z 279.2 (M+H)+.

Provenance & Evidence