Hydrogen Bromide → HCID 86656043, compound

Participants

Reaction Conditions

Reaction Steps

4-((3-methylpiperidin-3-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (52 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 10 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 an off-white solid (11 mg, 31%). 1H NMR (400 MHz, d6-DMSO) δ 12.18 (s, 1H), 8.70 (d, J=0.9, 1 H), 8.51 (d, J=0.9, 1 H), 8.27 (d, J=9.0, 1H), 6.90 (d, J=9.1, 1H), 4.48 (s, 1H), 3.93-3.84 (m, 1H), 3.64 (d, J=13.0, 1H), 3.55-3.40 (m, 2H), 1.79 (m, 1H), 1.67-1.57 (m, 2H), 1.52 (m, 1H), 1.13 (s, 3H). LCMS (Method E): RT=3.73 min, M+H+=308.2.

Provenance & Evidence