P-Toluenesulfonylhydrazide → HCID 59225698, compound

Participants

Reaction Steps

A 25 mL round-bottomed flask was charged with (E)-methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)acrylate (430 mg, 1.13 mmol), 4-methylbenzenesulfonohydrazide (1050 mg, 5.64 mmol) and toluene (10 mL). The reaction was heated to reflux for 12 hours. The reaction was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (20% EtOAc in hexanes) to afford the title compound (140 mg, 32.4% yield) as a white solid. 1H NMR (CDCl3) δ 8.49 (s, 1H), 7.80 (d, 1H), 7.41 (m, 5H), 7.00 (d, 1H), 6.37 (q, 1H), 5.08 (s, 2H), 3.67 (s, 3H), 2.89 (t, 2H), 2.61 (t, 2H), 2.31 (d, 3H). Mass spectrum (apci) m/z=384.1 (M+H).

Provenance & Evidence