Hydrogen Bromide → HCID 58365094, compound

Participants

Reaction Conditions

Reaction Steps

4-((1-ethyl-4-methylpiperidin-4-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (58 mg, 0.12 mmol) was dissolved in 1,4-dioxane (0.5 mL) and then treated with 48% HBr(aq) (0.5 mL) and heated at 75° C. for 15 minutes. The cooled reaction mixture was then basified to pH ˜12 by dropwise addition of 6N sodium hydroxide and then immediately acidified to pH ˜8-9 by dropwise addition of concentrated hydrochloric acid, producing a cloudy precipitate. The solid was collected by centrifugation, dissolved in dimethylsulfoxide (2 mL), and purified by preparative HPLC [5-85% methanol in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min] to afford the title compound as a white solid (13 mg, 30%). 1H NMR (400 MHz, d6-DMSO) δ 8.98 (d, J=0.8, 1H), 8.54 (d, J=5.7, 1H), 8.35 (d, J=0.8, 1H), 7.06 (d, J=5.8, 1H), 4.12 (s, 2H), 2.56 (m, 2H), 2.42-2.25 (m, 4H), 1.75 (m, 2H), 1.54 (m, 2H), 1.19 (s, 3H), 1.08-0.97 (m, 3H). LCMS (Method D): RT=8.49 min, M+H+=450.1.

Provenance & Evidence