2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one → 8-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

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Reaction Steps

A solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one (112f, 22 mg, 0.05 mmol) in TFA (2 mL) was stirred at room temperature for 24 hours. Volatiles were removed under vacuum and the residue was diluted in MeOH (1 mL). The solution was neutralized by 7N NH3 in MeOH (1.5 mL) and the product was purified by prep TLC (100% EtOAc) to afford the title compound as a white solid (Example 112, 8 mg, 50%). 1H NMR (400 MHz, DMSO-d6) δ 1.30 (s, 3H) 1.32 (s, 3H) 2.12 (s, 3H) 2.15 (s, 3H) 2.75 (t, J=6.17 Hz, 2H) 3.43 (t, J=6.17 Hz, 2H) 4.56 (s, 2H) 5.21-5.30 (m, 1H) 5.88 (s, 1H) 8.02 (s, 1H) 11.56 (br. s., 1H); MS 376.2 [M+1].

Provenance & Evidence