Hydrochloric Acid → HCID 73505856, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with (S) -1-(4-chloro-5-cyano-6-methylpyridin-2-yl)-3-(1-phenylethyl)urea (920 mg) and ethanol (6989 μl) and hydrazine (183 μl) was added. The reaction was heated to 95° C. for 17 hours. LC/MS showed the reaction was mostly but not entirely complete (˜15% remaining starting material by LC/MS integration). The reaction was heated for 5 additional hours. After cooling, HCl (1N, 14.6 mL) was added and the reaction was stirred for 30 minutes. The reaction was poured into a 500 mL separatory funnel containing 150 mL of concentrated sodium bicarbonate solution. The resulting emulsion was washed 3× with chloroform/IPA (4:1, 100 mL portions). The combined organic washings were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0-10% EtOAc/MeOH+0.1% ammonia) was performed and the active fractions were concentrated to dryness yielding the title compound as a white solid (400 mg, 41.1%). MS ESI calc'd for C16H18N6O [M+H]+ 311. found 311. 1H NMR (ppm500 Mhz, DMSO-d6): δ 9.30 (s, 1H), 8.74 (d, J=0.9 Hz, 1H), 8.29 (s, 1H), 8.07 (s, 1H), 7.37-7.32 (m, 5H), 7.28-7.21 (m, 1H), 6.60 (s, 2H), 4.88 (p, J=7.0 Hz), 2.47 (s, 3H), 1.42 (d, J=6.9 Hz, 3H).

Provenance & Evidence