Triethylamine → Adamantane-1-carboxylic acid{4,5-dimethyl-3-[2-(2,2,2-trifluoro-ethoxy)-ethyl]-3H-thiazol-2-ylidene}-amide

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Reaction Steps

To a solution of Example 85A (0.20 g, 0.8 mmol) in THF (10 mL) was added triethylamine (0.4 mL) and adamantane-1-carbonyl chloride (0.2 g, 1 mmol). The mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with 1M aqueous NaHCO3, dried (Na2SO4), filtered, and concentrated. Purification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes afforded 10 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.60-1.75 (m, J=28.8 Hz, 6 H), 1.83 (d, J=12.7 Hz, 6 H), 1.93-2.01 (m, 3 H), 2.15 (s, 3 H), 2.20 (s, 3 H), 3.92 (t, J=5.3 Hz, 2 H), 4.09 (q, J=9.5 Hz, 2 H), 4.28 (t, J=5.3 Hz, 2 H); MS (ESI+) m/z 417 (M+H)+; Anal. Calculated for C20H17F3N2O25: C, 57.67; H, 6.53; N, 6.73. Found: C, 57.53; H, 6.55; N, 6.69.

Provenance & Evidence