5-Chloro-2-methyl-1,8-naphthyridine → 2-(7-Methyl-[1,8]naphthyridin-4-ylamino)-biphenyl-4-carboxylic acid methyl ester

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Reaction Steps

The product from Example 1d (0.0552 g, 0.309 mmol) was reacted with the product from Example 212c (0.070 g, 0.309 mmol) for 92 h following the procedure of Example 1g giving the crude title compound, which was purified by HPLC with AA. The resulting solid was triturated with 4N HCl in dioxane to generate the hydrochloride salt which was collected by vacuum filtration (0.0747 g, 55%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.72 (s, 3H) 3.91 (s, 3H) 6.27 (d, J=6.99 Hz, 1H) 7.30 (m, J=6.99 Hz, 3H) 7.52 (m, 2H) 7.74 (d, J=8.82 Hz, 1H) 7.79 (d, J=8.09 Hz, 1H) 8.09 (d, J=1.47 Hz, 1H) 8.16 (dd, J=7.91, 1.65 Hz, 1H) 8.30 (d, J=6.99 Hz, 1H) 9.15 (d, J=8.82 Hz, 1H) 11.54 (s, 1H); MS (ESI+) m/z 369.9 (M+H)+.

Provenance & Evidence