2-Amino-2-methyl-1-propanol → 2-{[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]amino}-2-methylpropan-1-ol

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Reaction Conditions

Reaction Steps

3-(4-Bromophenyl)-5-chloro-1,2,4-thiadiazole (2.0 g, 7.3 mmol), prepared in the previous step, was dissolved in 2-amino-2-methylpropanol and heated to 125° C. for 16 h. The mixture was cooled, diluted with ethyl acetate, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10% acetone in hexane) afforded 2-{[3-(4-bromophenyl)-1,2,4-thiadiazol-5-yl]amino}-2-methylpropan-1-ol (0.85 g, 35%) as a pale yellow solid. HRMS: calcd for C12H14BrN3OS+H+, 328.01137; found (ESI, [M+H]+), 328.0113; Analytical HPLC: purity 100% at 210-370 nm, 10.0 min; 100% at 252 nm, 10.0 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH 3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence