3-Pyridinemethanamine → 4-Amino-5-cyano-n-(pyridin-3-ylmethyl)-6-thien-3-ylpyridine-2-carboxamide

Participants

Reaction Steps

To a mixture of Example 266A (12 mg, 0.05 mmol), C-pyridin-3-yl-methylamine (6 μL, 0.1 mmol) in N,N-dimethylformamide (400 μL) was added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (17 mg, 0.053 mmol), followed by N,N-diisopropylethylamine (17 μL). The reaction mixture was stirred at ambient temperature for 3 hr. It was diluted with 1 mL acetonitrile and purified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to provide the titled compound as white solid (98 mg, 48%). 1H NMR (300 MHz, DMSO-d6) δ 9.35 (t, J=6.4 Hz, 1H), 8.56-8.38 (m, 3H), 7.93-7.90 (m, 1H), 7.74-7.66 (m, 2H), 7.40-7.32 (m, 3H), 7.36 (s, 1H), 4.52 (d, J=6.4 Hz, 2H). MS (m/e) 336 (M+H)+.

Provenance & Evidence