N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine → HCID 178490986, compound

Participants

Reaction Steps

To a vial charged with N-(4-methoxybenzyl)thiazol-2-amine (655 mg, 2.97 mmol) was added THF (6940 μl) and the mixture cooled in an ice water bath prior to the addition of lithium bis(trimethylsilyl)amide, 1.0M solution in tetrahydrofuran (3185 μl, 3.19 mmol), faster than drop wise. After 15 mins of stirring, a solution of 4-bromo-3-hydroxyisoquinoline-7-sulfonyl chloride (685 mg, 2.124 mmol) in THF (4 mL) was added drop wise (with 1 mL THF wash). The mixture was stirred for 1.5 hr (ice melt), LCMS indicated complete conversion to the desired product. The solution was added to ice, diluted with EtOAc and extracted with water and EtOAc. The combined organics were dried with Na2SO4, filtered, and dried under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 60% EtOAc in hexane, to provide 4-bromo-3-hydroxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-7-sulfonamide. m/z (ESI) 506.0 (M+H)+

Provenance & Evidence