Hydrochloric Acid → 2-(4-((2-Bromoethoxy)(methoxy)methyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol

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Reaction Steps

To a vial containing 2-(4-(dimethoxymethyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol (50 mg), 2-bromoethanol (1 mL) and a solution of HCl in dioxane (125 uL of 4M) was added. After 4 hours at room temperature, an aqueous solution of triethylammonium acetate (TEAA) (1 mL of 1M) was added to the reaction. After filtration, the solution was purified by preparative RP-HPLC by eluting with 50 mM TEAA ramping to acetonitrile over 30 min. Yield 26 mg. 1H NMR (300 MHz, CDCl3) δ 7.96 (d, J=8.9, 1H), 7.33 (d, J=2.4, 1H), 7.06 (dd, J=2.3, 8.9, 1H), 4.88 (dt, J=6.8, 13.2, 1H), 4.79-4.67 (m, 1H), 4.16-3.73 (m, 3H), 3.64-3.38 (m, 8H), 1.36 (dd, J=2.4, 5.3, 1H). mass spectrum, calculated (MH+) 304/306. found 304/306

Provenance & Evidence