N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine → HCID 86687723, compound

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Reaction Steps

A round-bottom flask was charged with N-(4-methoxybenzyl)thiazol-2-amine (63.5 mg, 0.288 mmol) and THF (1.60 mL) to give a clear solution. The flask was cooled in a dry ice-acetone bath for 5 min to give a suspension. Lithium bis(trimethylsilyl)amide (1M in THF, 961 μl, 0.961 mmol) was added drop wise to give a light yellow solution. The mixture was stirred for 15 min. Then, a solution of perfluorophenyl 1-(5-chloro-2-methoxyphenyl)-4-oxo-3,4-dihydrophthalazine-6-sulfonate (128 mg, 0.240 mmol) in THF (1.60 mL)) was added drop wise. LCMS after 1 h showed a complete conversion of SM to mainly product. The reaction was quenched with saturated aqueous ammonium chloride (0.5 mL) at −78° C. and then warmed to rt. The product was extracted with EtOAc. The organic layers was dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 20-50% EtOAc/heptanes) to give 1-(5-chloro-2-methoxyphenyl)-N-(4-methoxybenzyl)-4-oxo-N-(thiazol-2-yl)-3,4-dihydrophthalazine-6-sulfonamide (56 mg, 41.0% yield) as an off-white solid. m/z (ESI) 569.0 (M+H)+.

Provenance & Evidence