Hydrogen Peroxide → HCID 71522868, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(4,6-dimethylpyridin-2-yl)amino]benzonitrile (70 mg, 0.21 mmol) and sodium hydroxide (4.0 M in water, 0.25 mL, 1.0 mmol) in DMSO (2.5 mL) was added hydrogen peroxide (30% aqueous solution, 0.10 mL, 0.98 mmol). The reaction mixture was heated to 35° C. After 40 minutes, the reaction mixture was filtered and purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to give rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(4,6-dimethylpyridin-2-yl)amino]benzamide. MS ESI calc'd. for C20H28N5O [M+H]+ 354. Found 354. 1H NMR (300 MHz, CD3OD) δ 7.67 (s, 1H), 7.47 (d, J=8.7 Hz, 1H), 6.55 (m, 2H), 6.21-6.25 (m, 1H), 3.55-3.52 (m, 1H), 3.17 (br s, 1H), 2.37 (s, 3H), 2.22 (s, 3H), 1.77-1.42 (m, 8H).

Provenance & Evidence