Diisopropylethylamine → Trifluoroacetic acid

Participants

Reaction Steps

To a mixture of the product from Example 54F (30 mg, 0.115 mmol) and 4-(trifluoromethyl)picolinic acid (26.4 mg, 0.138 mmol) in dichloromethane (1 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (33.1 mg, 0.173 mmol) followed by 1-hydroxybenzotriazole hydrate (26.5 mg, 0.173 mmol) and Hunig's base (0.040 mL, 0.230 mmol). The resulting solution was stirred at ambient temperature for 90 minutes. The mixture was partitioned between water (1 mL) and dichloromethane (3×1 mL), and the combined dichloromethane layers were concentrated in vacuo. The crude product was purified by column chromatography on C-18 reverse-phase silica gel using a solvent gradient of 0-100% acetonitrile in water (0.1% trifluoroacetic acid). The fractions containing pure product were pooled and concentrated in vacuo to give the title compound as a trifluoroacetic acid salt. 1H NMR (300 MHz, CDCl3) δ ppm 5.55-5.65 (m, 1 H), 7.65 (d, J=5.16 Hz, 1 H), 7.90-8.00 (m, 1 H), 8.03-8.13 (m, 2 H), 8.77 (t, J=5.35 Hz, 1 H); MS (ESI) m/z 434.1 (M+H)+.

Provenance & Evidence