Hydrogen Bromide → HCID 58365077, compound

Participants

Reaction Conditions

Reaction Steps

(R)-4-(1-ethylpiperidin-3-oxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (46 mg, 0.10 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 (12 mg, 37%). 1H NMR (400 MHz, d6-DMSO) δ 12.78 (s, 1H), 8.96 (d, J=0.9, 1H), 8.54-8.51 (d, J=5.9, 1H), 8.50 (d, J=0.9, 1H), 7.11 (d, J=5.9, 1H), 4.93-4.83 (m, 1H), 2.98 (d, J=8.9, 1 H), 2.61 (m, 1H), 2.52 (m, 2H), 2.44 (q, J=7.2, 2H), 2.26 (t, J=8.8, 1H), 2.07 (m, 1H), 1.86-1.75 (m, 1H), 1.66 (m, 2H), 1.04 (t, J=7.1, 3H). LCMS (Method E): RT=7.33 min, M+H+=322.1.

Provenance & Evidence