Sodium Hydroxide → HCID 59375650, compound

Participants

Reaction Conditions

Reaction Steps

9-Iodo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (130 mg, 0.31 mmol), copper(I) iodide (5.9 mg, 0.031 mmol), L-proline (7.1 mg, 0.062 mmol), sodium hydroxide (2.5 mg, 0.062 mmol), and methanesulfinic acid sodium salt (41 mg, 0.40 mmol) were combined in a vial. DMSO (2.0 ml) was added, and the resulting suspension was purged with argon (subsurface bubbling) for 5 min. The reaction mixture was stirred at 95° C. for 24 h. The crude material was precipitated out of solution by adding 2 mL of MeOH, followed by 1.5 mL of water. The solids were collected by vacuum filtration, and purified by preparative reverse phase HPLC, eluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient, to afford 9-(methylsulfonyl)-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (500 MHz, DMSO-D6) δ 11.33 (br s, 1H), 10.45 (s, 1H), 8.74 (d, 1H), 8.01 (dd, 1H), 7.59 (br d, 1H), 7.36 (d, 1H), 6.36 (d, 1H), 4.71 (pentet, 1H), 3.25 (s, 3H), 1.17 (d, 3H), 0.93 (s, 9H). LRMS (ESI) calc'd for (C19H23N3O3S) [M+H]+, 374.1; found 374.1.

Provenance & Evidence