Hydrogen Bromide → HCID 58365138, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-(3-(2,2,2-trifluoroethylamino)pyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (156 mg, 0.32 mmol) was dissolved in 1,4-dioxane (0.4 mL) and then treated with 48% HBr(aq) (0.4 mL) and heated at 60° C. for 20 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 yellow solid (5.0 mg, 5%). 1H NMR (400 MHz, d6-DMSO) δ 8.81 (s, 1H), 8.47 (s, 1H), 8.15 (d, J=5.8, 1H), 6.43 (d, J=5.8, 1H), 3.95 (m, 1H), 3.81 (m, 1H), 3.68 (m, 1H), 3.60-3.50 (m, 2H), 2.81 (m, 1H), 2.14 (m, 1H), 2.02-1.88 (m, 1H). LCMS (Method D): RT=7.71 min, M+H+=361.0.

Provenance & Evidence