Hydrogen Bromide → HCID 53250700, compound

Participants

Reaction Conditions

Reaction Steps

(R)-4-(1-methylpiperidin-3-yloxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (93 mg, 0.21 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 (18 mg, 27%). 1H NMR (400 MHz, d6-DMSO) δ 12.74 (s, 1H), 8.96 (d, J=0.8, 1H), 8.52 (d, J=5.8, 1H), 8.46 (d, J=0.9, 1H), 7.10 (d, J=5.9, 1H), 4.93-4.82 (m, 1H), 2.93 (m, 1H), 2.57-2.51 (m, 1H), 2.44 (m, 1H), 2.24 (s, 3H), 2.19 (m, 1H), 2.08 (m, 1H), 1.83 (m, 1H), 1.68 (m, 2H). LCMS (Method D): RT=7.08 min, M+H+=308.1.

Provenance & Evidence