Cyanogen Bromide → HCID 178436509, compound

Participants

Reaction Steps

To 6-(benzyloxy)-N2-(4-ethylphenyl)pyridine-2,3-diamine (358 mg, 1.12 mmol) was added H2O (3.0 mL) and cyanogen bromide (178 mg, 1.68 mmol). The mixture was stirred vigorously at room temperature overnight. Saturated NaHCO3 was added and the mixture was extracted with EtOAc. After concentration in vacuo, the crude material was dissolved in MeOH (5 mL) and ammonium formate (353 mg, 5.6 mmol) was added. Pd/C (10% by wt., 100 mg) was added and the mixture was stirred in a sealed vial at 60° C. overnight. The reaction mixture was cooled to room temperature, filtered through celite, and concentrated. The residue was purified by preparative HPLC to give the title compound (14.4 mg) as a white solid. LCMS m/z=255.3, [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (t, J=7.6 Hz, 3H), 2.73 (q, J=7.6 Hz, 2H), 6.54 (d, J=8.5 Hz, 1H), 7.49 (d, J=8.5 Hz, 2H), 7.53 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.5 Hz, 1H), 8.32 (broad s, 2H), 10.91 (broad s, 1H).

Provenance & Evidence