Hydrochloric Acid → 2-[4-(2-acetylamino-4-methyl-thiazole-5-sulfonylamino)-phenyl]-N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-(4-amino-phenyl)-acetamide (prepared as in Example 1, 75 mg, 0.16 mmol) in pyridine (1.6 mL) was stirred at 25° C. for 5 min. This solution was then treated with 2-acetylamino-4-methyl-thiazole-5-sulfonyl chloride (44 mg, 0.17 mmol). The reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was then poured into a mixture of methylene chloride (50 mL) and a 1.0N aqueous hydrochloric acid solution (10 mL). This mixture was extracted with a 1/9 methanol/methylene chloride solution (1×50 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 7/93 methanol/methylene chloride) afforded 2-[4-(2-acetylamino-4-methyl-thiazole-5-sulfonylamino)-phenyl]-N-[6-amino-1-cyclopropylmethyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide (56.4 mg, 54%) as an off-white solid; FAB-HRMS m/e calculated for C29H30FN7O6S2 (M+) 655.1683, found 655.1679

Provenance & Evidence