Sodium borohydride → N-(4-{2-[7-(2-Hydroxy-ethyl)-[1,8]naphthyridin-4-ylamino]-4-methyl-phenylsulfanyl}-phenyl)-acetamide

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Reaction Steps

The product from Example 23b (56 mg, 0.10 mmol) was reacted with NaBH4 (40 mg, 1.00 mmol) in 5 mL EtOH for 24 h. Quenched with aqueous NH4Cl and adjusted to pH 7 with dilute HCl. Extracted with EtOAc and dried over Na2SO4, filtered and concentrated under vacuum giving the crude title compound which was purified by HPLC with TFA giving the trifluoroacetic acid salt (15 mg, 25%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.04 (s, 3 H) 2.35 (s, 3 H) 3.16 (t, J=6.43 Hz, 2 H) 3.91 (t, J=6.25 Hz, 2 H) 6.31 (d, J=6.99 Hz, 1 H) 7.14 (d, J=8.09 Hz, 1 H) 7.22-7.33 (m, 4 H) 7.51 (d, J=8.82 Hz, 2 H) 7.83 (d, J=8.82 Hz, 1 H) 8.42 (d, J=6.99 Hz, 1 H) 8.94-9.05 (m, 1 H) 10.04 (s, 1 H) 11.03 (s, 1 H) 14.40 (s, 1 H); MS (ESI+) m/z 445 (M+H−TFA)+.

Provenance & Evidence