Formaldehyde → HCID 118036629, compound

Participants

Reaction Steps

A mixture of 1-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-3,3-dimethylpiperazin-2-one (intermediate 304, 100 mg, 0.287 mmol), formaldehyde (36.5% in water, 22 μl, 0.290 mmol) and triethylamine (100 μl, 0.721 mmol) in MeOH (2 ml) was stirred at room temperature for 22 days before being partitioned between aqueous saturated NaHCO3 and DCM, extracting 2× with DCM, the combined organic layers dried over Na2SO4 and evaporated. The crude material was preabsorbed onto isolate and purified by normal phase chromatography: 4 g RediSep column, eluting with a gradient from DCM to 95:5 DCM:MeOH containing 1% NH3. The product containing fractions were combined and evaporated to give the title compound as a colourless glass. 1H NMR (400 MHz, CDCl3) δ 7.03 (s, 1H), 5.21 (s, 1H), 4.65 (s, 2H), 3.42-3.35 (m, 8H), 3.20-3.13 (m, 2H), 2.72 (t, 2H), 2.67 (t, 2H), 2.33 (s, 3H), 1.87 (m, 2H), 1.36 (s, 6H).

Provenance & Evidence