Triethylamine → HCID 9954774, compound

Participants

Reaction Steps

To a solution of 3-[1-phenyl-1-(tetrahydropyran-2-yloxy)methyl]-5-chloro-[1,2,4]thiadiazole (3.11 g, 10 mmol) in DMF (50 mL) was added 1-(2-pyridyl)piperazine (3.26 g, 20 mmol) dissolved in DMF (5 mL) followed by triethylamine (4.04 g, 40 mmol). The resulting mixture was stirred at room temperature for 30 min then diluted with water (150 mL) and ethyl acetate (150 mL). The organic layer was collected, washed with water (100 mL), dried (sodium sulfate), filtered and concentrated in vacuo. Purification by column chromatography on silica gel using a solvent gradient of a mixture of hexane and ethyl acetate (7/3 and 1/1) afforded 1 -{3-[phenyl-(tetrahydropyran-2-yloxy) methyl]-[1,2,4]thiadiazol -5-yl}4-pyridin-2-yl-piperazine (4.31 g, 98.4%) as a colorless foam and as a mixture of diastereoisomers. 1H-NMR (CDCl3) δ8.22 (d, J=4.6 Hz, 1H, Py-H), 7.51-7.58 (m, 3H), 7.27-7.39 (m, 3H), 6.68-6.71 (m, 2H), 5.93 and 5.88 (s, 0.5H each, αH), 4.91 and 4.67 (t, J=3.2 Hz, 0.5H each, OCHO), 3.51-4.02 (m, 2H, OCH2), 3.69-3.71 (m, 4H, 2CH2), 3.63-3.64 (m, 4H, 2CH2), 1.51-1.97 (m, 6H, 3CH2).

Provenance & Evidence