HCID 67065563, compound → HCID 49838261, compound

Participants

Reaction Steps

4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenyl dibenzyl phosphate (1.0 equiv.) and 10% Pd/C (20% equiv. by weight) in MeOH (0.66 M) was allowed to stir for 18 hours under a balloon of H2. At this point the reaction mixture was passed through a pad of Celite, washing with a 2:1 mixture of CHCl3:MeOH. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by Reverse Phase-HPLC using a 20-90% 0.5 mM NH4OAc (in MeCN) to 10 mM NH4OAc (in water) gradient to give 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenyl dihydrogen phosphate (2) as a solid. TFA was added to the 1H NMR sample to solubilize the compound for analysis. 1H NMR (Dimethylsulfoxide-d6): δ 9.69 (br, 1H), 9.33 (s, 1H), 9.03 (s, 1H), 8.87 (s, 1H), 8.54 (d, 1H, J=8.4 Hz), 7.51 (s, 1H), 7.42 (d, 1H, J=9.4 Hz), 7.22 (s, 1H), 7.17 (d, 1H, J=8.3 Hz), 7.10 (s, 1H), 6.97 (s, 1H), 6.92 (d, 1H, J=6.1 Hz), 3.15 (t, 2H, J=6.8 Hz), 3.00 (t, 2H, J=6.8 Hz), 2.50 (s, 3H), 2.29 (s, 3H). LRMS [M+H]=424.1

Provenance & Evidence