Benzylamine → HCID 22921561, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution of 0.7 gram (0.0015 mole) of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propanoic acid (Compound 19--prepared as in Step B of Example 8) in 20 mL of methylene chloride was stirred, and 0.4 gram (0.0030 mole) of 1-hydroxybenzotriazole, then 0.5 gram (0.0030 mole) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. The reaction mixture was cooled to about 0° C., and 0.2 gram (0.0015 mole) of N-(phenylmethyl)amine was added. Upon completion of the addition, the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 72 hours. The reaction mixture was then poured into water and extracted with methylene chloride. The combined extracts were washed with an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil, which was subjected to column chromatography on silica gel, with 1:2 ethyl acetate/hexane as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.5 gram of N-phenylmethyl-2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propanecarboxamide; mp 191°-193° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence