Tetrabutylammonium Fluoride → HCID 118036952, compound

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A solution of (racemic) 4-((tert-butyldiphenylsilyl)oxy)-N-(5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 37Y, 30 mg, 0.049 mmol) in THF (0.3 ml) was treated with TBAF (1 M in THF, 0.054 ml, 0.054 mmol) and stirred at room temperature for 2 h. The reaction mixture was partitioned between DCM and sat. aq. NaHCO3. The aq. layer was extracted with DCM (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 10:90) to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.93 (s, 1H), 8.76-8.81 (m, 1H), 8.19-8.27 (m, 2H), 7.95 (d, 1H), 7.26 (d, 1H), 5.71 (d, 1H), 5.39 (s, 1H), 4.67-4.75 (m, 1H), 3.96-4.01 (m, 2H), 3.38 (d, 6H), 2.01-2.10 (m, 1H), 1.79-1.90 (m, 1H).

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