4-(Chloromethyl)pyridine → Adamantane-1-carboxylic acid(4,5-dimethyl-3-pyridin-4-ylmethyl-3H-thiazol-2-ylidene)-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 97A (145 mg, 0.50 mmol) in DMF (5 mL) was added potassium tert-butoxide (120 mg, 1.10 mmol) and the hydrochloride salt of 4-chloromethyl-pyridine (82 mg, 0.5 mmol). The mixture was heated in a SmithSynthesizer™ microwave at 250° C. for 15 minutes. The mixture was diluted with ethyl acetate, washed with 1M NaHCO3, and layers were separated. The aqueous layer was extracted with methylene chloride (3×). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was recrystallized from ethyl acetate to afford the title compound (70 mg, 36%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.54-1.72 (m, 6 H), 1.75 (d, J=2.4 Hz, 6 H), 1.91 (s, 3 H), 2.09 (d, J=0.7 Hz, 3 H), 2.17 (d, J=0.7 Hz, 3 H), 5.44 (s, 2 H), 7.06-7.20 (m, 2 H), 8.50-8.56 (m, J=6.1 Hz, 2 H); MS (ESI+) m/z 382 (M+H)+; Anal. Calculated for C22H27N3OS.0.2H2O: C, 68.61; H, 7.17; N, 10.91. Found: C, 68.56; H, 7.12; N, 10.76.

Provenance & Evidence