Chloroacetyl chloride → 2-Chloro-N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide

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Reaction Steps

A mixture of 2-(2,4,6-trimethyl-phenoxy)-N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine (250 mg, 0.76 mmol) and triethylamine (0.11 ml, 0.76 mmol) in 5 ml of dry THF was treated with chloroacetyl chloride (0.06 ml, 0.76 mmol) at 0° C. The resulting mixture was stirred at room temperature for 1 hour. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 310 mg of green crystals that was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 280 mg (90%) of the title compound as tan crystals, mp 152-154° C. 1H NMR (CDCl3) δ 8.07(s,1H), 6.88(s,2H), 6.16(s,1H), 4.75(brs,1H), 4.25(s,2H), 3.33(m,1H), 2.30(s,3H), 2.18(s,3H), 2.08(s,6H), 1,4-1.8(m,4H), 0.97(t,6H) ppm.

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