HCID 59605558, compound → HCID 59606157, compound

Participants

Reaction Steps

A 50 mL round-bottomed flask, under nitrogen, fitted with a condenser/inert gas bubbler (via a Claisen head), was charged with a solution of 2-{1-[2-(1-benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-c]pyridin-4-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl]piperidin-4-yl}propan-2-ol (0.41 g, 0.64 mmol) in dioxane (8 mL), IMS (8 mL) and NaOH 12.5M (0.8 mL). The resulting mixture was stirred at room temperature for 2 h. The solution was concentrated in vacuo, the residue was dissolved in DCM and a fine solid was removed by filtration through a Celite pad. The solution was purified by flash chromatography (Si—PCC; 25 g SiO2 column, 0% to 20% MeOH in DCM). The residue was then purified further by preparative HPLC [(C18 column) gradient: (acetonitrile/20 mM triethylamine) 30% to 98% in (water/20 mM triethylamine) over 20 min (flow rate 18 ml/min)]. The product was freeze-dried overnight yielding 165 as a white powder (0.136 g, 43%). LCMS (method E): RT=4.89 min, [M+H]+ 505.24. 1H NMR (CDCl3, 400 MHz) δ 9.28 (s, 1 H), 8.70 (s, 1 H), 8.30 (s, 1 H), 4.40 (m, 4 H), 3.96 (s, 3 H), 3.89 (m, 4 H), 3.74 (s, 2 H), 2.96 (m, 2 H), 2.58 (s, 3 H), 2.10 (m, 2 H), 1.75 (m, 2 H), 1.40-1.28 (m, 3 H), 1.18 (s, 6 H)

Provenance & Evidence