4-Chloro-1,8-naphthyridine → 4-[4-(4-Fluoro-benzyloxy)-2-([1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

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Reaction Steps

The product from Example 16c (50 mg, 0.30 mmol) was reacted with the product from 4-[2-amino-4-(4-fluoro-benzyloxy)-phenylsulfanyl]-phenol (102 mg, 0.30 mmol) for 20 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (99 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 5.11 (s, 2 H) 6.31 (d, J=6.99 Hz, 1 H) 6.64 (d, J=8.45 Hz, 2 H) 7.08-7.27 (m, 6 H) 7.50 (m, J=5.51 Hz, 2 H) 7.91 (d, J=4.41 Hz, 1 H) 8.47 (d, J=6.98 Hz, 1 H) 9.13 (dd, J=1.47 Hz, J=8.45 Hz, 1 H) 9.17 (dd, J=1.47 Hz, J=4.05 Hz, 1 H) 9.79 (s, 1 H) 11.14 (br s,1 H) 14.50 (br s,1 H); MS (ESI+) m/z,470 (M+H−TFA)+; (ESI−) m/z, 468 (M−H−TFA)−.

Provenance & Evidence