Pyridine → HCID 68874736, compound

Participants

Reaction Steps

To a solution of the resulting alcohol (55 mg, 0.31 mmol) and pyridine (33 μL, 0.37 mmol) in dichloromethane (0.5 mL) at 0° C. was added methanesulfonyl chloride (43 mg, 0.37 mmol). After 1 hour at room temperature, the mixture was diluted with 10 mL ethyl acetate. The organic layer was washed with 2× dilute aqueous ammonium chloride (5 mL), 2× brine (5 mL), dried over magnesium sulfate, filtered and evaporated. The residue was dissolved in N,N-dimethylformamide (1 mL) and treated with 1-pyridin-2-ylpiperazine (48 μL, 0.31 mmol) and N,N-diisopropylethylamine (155 μL, 0.78 mmol). After 24 hours at 100° C., the mixture was cooled and concentrated. The residue was purified by flash column chromatography on silica gel (elution with 1-2.5% methanol:dichloromethane) to provide 45 mg (45% yield) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.40 (s, 3H), 2.66 (m, 6H), 3.60 (m, 6H), 6.65 (m, 2H), 6.84 (s, 1H), 7.31 (m, 2H), 7.49 (ddd, J=8.7, 7.0, 2.0 Hz, 1H), 7.55 (m, 1H), 7.63 (s, 1H), 8.20 (ddd, J=5.0, 2.0, 0.9 Hz, 1H); MS (DCI/NH3) m/e 325 (M+H)+; Anal. calcd for C19H24N4O.0.2 H2O: C, 69.57; H, 7.50; N, 17.08. Found: C, 69.41; H, 7.21; N, 17.10.

Provenance & Evidence