Hydrochloric Acid → 5-(2-chloropyridin-4-ylthio)-N-(4-methylthiazol-2-yl)-3-phenoxypyridin-2-amine dihydrochloride

Participants

Reaction Steps

A mixture of methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (72 mg, 0.18 mmol), 2-chloro-4-nitropyridine (85.3 mg, 0.54 mmol) and DMSO (2.0 mL) and purged with nitrogen for 5 minutes. Potassium 2-methylpropan-2-olate (60.4 mg, 0.54 mmol) was added and stirred for 30 minutes. The reaction was poured into aqueous NH4Cl and extracted with EtOAc (1×20 mL). The organic phase was washed with water, dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (25% EtOAc in hexanes) to afford the title compound (37.1 mg, 41.4% yield) as a white solid after HCl salt formation. 1H NMR (CDCl3) δ 12.89 (bs, 1H), 8.24 (m, 2H), 8.17 (d, 1H), 7.43 (t, 2H), 7.31 (d, 1H), 7.28-7.18 (m, 3H), 6.88 (s, 1H), 6.84 (m, 1H), 6.53 (s, 1H), 3.93 (s, 1H), 2.50 (s, 3H). Mass spectrum (apci) m/z=427.2 (M+H-2HCl).

Provenance & Evidence