Triethylamine → 5-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-amine

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Reaction Steps

Ethanesulfonyl chloride (62.13 mg, 45.78 μL, 0.4832 mmol) and triethyl amine (122.2 mg, 168.3 μL, 1.208 mmol) were added to a solution of 3-(5-phenyl-1,2,4-oxadiazol-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine (129 mg, 0.4027 mmol) in dichloromethane (5 mL) at 0° C. and the resulting solution stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried. The solid was taken up in dichloromethane (5 mL) and washed with saturated aqueous NaHCO3 solution (2×5 mL), dried over MgSO4 and concentrated in vacuo to leave the product (65 mg, 40% yield) 1H NMR (400 MHz, DMSO) d 1.24 (t, 3H), 2.68 (m, 2H), 3.13 (q, 2H), 3.48 (m, 2H), 3.99 (m, 2H), 6.63 (m, 1H), 7.29 (br s, 2H), 7.68 (m, 2H), 7.77 (m, 1H), 8.26 (m, 2H) and 8.52 (1H, s) ppm; MS (ES+) 412.97

Provenance & Evidence