Trifluoroacetic acid → 3-fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propenyl)-naphthalen-1-yl]-benzamide

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Reaction Steps

[4-(3-Morpholin-4-yl-propenyl)-naphthalen-1-yl]-carbamic acid tert-butyl ester (367 mg, 1.0 mmol) is stirred at room temperature in dichloromethane (10 ml) and trifluoroacetic acid (5 ml) for 2 hours. The mixture is then evaporated to dryness. The residue, 3-fluoro-5-morpholinyl benzoic acid (337 mg, 1.5 mmol), HBTU (758 mg, 2.0 mmol) and diisopropylethylamine (0.87 ml, 5.0 mmol) are stirred at room temperature in a mixture of tetrahydrofuran (5 ml) and dimethylformamide (1 ml) for 16 hours. The mixture is then poured into ethyl acetate (100 ml) and washed with water (100 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluted with 50% ethyl acetate in hexanes followed by 2.5% methanol in ethyl acetate to give 3-fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propenyl)-naphthalen-1-yl]-benzamide as a pale yellow oil (56 mg).

Provenance & Evidence