Potassium trimethylsilanolate → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(6-ethylpyridin-2-yl)amino]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(6-ethylpyridin-2-yl)amino]pyridine-2-carbonitrile (51 mg, 0.152 mmol) and potassium trimethylsilanolate (486 mg, 3.79 mmol) in dioxane (3 mL) was heated to 100° C. for 3 hours. The reaction mixture was allowed to cool to room temperature, filtered, and concentrated under reduced pressure. The residue was dissolved in DMSO, filtered, and purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(6-ethylpyridin-2-yl)amino]pyridine-2-carboxamide. MS ESI calc'd. for C19H27N6O[M+H]+ 355. found 355. 1H NMR (500 MHz, DMSO-d6) δ 11.84 (s, 1H), 8.56 (s, 1H), 7.92 (s, 1H), 7.88-7.80 (m, 2H), 7.70 (d, J=2.5 Hz, 1H), 7.58-7.54 (m, 1H), 7.34 (s, 1H), 6.76 (d, J=7.3 Hz, 1H), 6.65 (d, J=8.2 Hz, 1H), 6.34 (d, J=8.4 Hz, 1H), 3.81 (br s, 1H), 2.68 (q, J=7.5 Hz, 2H), 1.86-1.79 (m, 2H), 1.73-1.67 (m, 1H), 1.67-1.54 (m, 3H), 1.45-1.35 (m, 2H), 1.24 (t, J=7.6 Hz, 3H).

Provenance & Evidence