Triethylamine → HCID 59375549, compound

Temperature

120 °C

To a solution of 9-bromo-1,6-dichloro-3-methyl-benzo[c][1,6]naphthyridine (0.12 g, 0.35 mMol) in anhydrous dioxane (4 mL) was added anhydrous Et3N (0.07 mL, 0.53 mMol), followed by 2-aminomethylpyridine (0.038 g, 0.35 mMol). The resulting reaction mixture was heated in a sealed tube at 120° C. for 5 hours. The reaction mixture was concentrated to a crude solid that was redissolved in EtOAc (10 mL). The EtOAc layer was washed with water (2×5 mL), brine (1×10 mL) and dried over MgSO4. The filtrate was concentrated and the resulting residue was purified by flash chromatography using an EtOAc/Hexanes gradient to afford 9-bromo-1-chloro-3-methyl-N-(pyridin-2-ylmethyl)benzo[c]-1,6-naphthyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) 9.88 (d, 1H), 8.65 (bs, 1H), 7.97 (d, 1H), 7.83-7.80 (dd, 1H), 7.75 (t, 1H), 7.64 (bs, 1H), 7.43 (s, 1H), 7.41 (s, 1H), 7.27 (s, 1H), 4.99 (d, 2H), 2.62 (s, 3H). LRMS calculated for C19H14BrClN4 [M+H]+, 415.0; found 415.1.

1. customThe resulting reaction mixture
2. concentrationThe reaction mixture was concentrated to a crude solid
3. dissolutionthat was redissolved in EtOAc (10 mL)
4. washThe EtOAc layer was washed with water (2×5 mL), brine (1×10 mL)
5. dry with materialdried over MgSO4
6. concentrationThe filtrate was concentrated
7. customthe resulting residue was purified by flash chromatography

ORD record

ord-b003379bfa8f48f4a311fadafb90e626

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329722B2