Triethylamine → 3-amino-6-(1-(ethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-N-(2-methylpyridin-4-yl)pyrazine-2-carboxamide

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Reaction Conditions

Reaction Steps

A solution of 3-amino-6-(1-ethylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazine-2-carboxylic acid (79.87 mg, 0.255 mmol), CDI (82.92 mg, 0.511 mmoles), triethylamine (107 uL, 0.767 mmoles), and DMAP (1.56 mg, 0.012 mmol) was treated with 2-methylpyridin-4-amine (55.30 mg, 0.511 mmol). The reaction was allowed to stir at 100° C. for 16 hours, filtered 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 to give the title compound (30.4 mg, 21% Yield). 1H NMR (400.0 MHz, DMSO) d 11.10 (s, 1H), 8.69-8.67 (m, 2H), 8.25-8.22 (m, 2H), 7.72 (s, 2H), 6.77 (d, J=3.3 Hz, 1H), 3.99 (d, J=2.9 Hz, 2H), 3.48 (t, J=5.7 Hz, 2H), 3.16 (q, J=7.4 Hz, 2H), 2.79 (s, 2H), 2.68 (s, 3H) and 1.25 (t, J=7.3 Hz, 3H) ppm; MS (ES+) 403.0

Provenance & Evidence