Ethanol → 4-[4-Phenoxymethyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Participants

Reaction Conditions

Reaction Steps

The product from Example 2g as a 4.1M solution in ethanol (0.050 mL, 0.205 mmol) was reacted with the product from Example 221d (0.066 g, 0.205 mmol) for 16.5 h following the procedure from Example 1g. Consumption of starting material required a second addition of the product from Example 2g (0.025 mL, 0.102 mmol) and continued heating at 80° C. (12 h). The crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.0269 g, 21.5%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.54 Hz, 3 H) 1.76-1.99 (m, 2H) 3.00 (t, J=7.35 Hz, 2 H) 5.12 (s, 2 H) 6.31 (d, J=6.99 Hz, 1 H) 6.79 (d, J=8.82 Hz, 2 H) 6.91-7.07 (m, 4 H) 7.17-7.37 (m, 4 H) 7.43-7.55 (m, 2 H) 7.84 (d, J=8.82 Hz, 1 H) 8.47 (d, J=7.35 Hz, 1 H) 9.04 (d, J=8.46 Hz, 1 H) 9.97 (s, 1 H); MS (ESI+) m/z 494.2 (M+H)+; (ESI−) m/z 492.2 (M−H)−.

Provenance & Evidence