Hydrochloric Acid → HCID 178437410, compound

Participants

Reaction Steps

To a solution of 4-{1-[2-(2-ethylbenzoimidazol-1-yl)-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purin-8-ylmethyl]azetidin-3-yl}piperazin-2-one (470 mg, 0.78 mmol) in dioxane (20 mL) was added 4M HCl in dioxane (1 mL). The resulting suspension was stirred at r.t for 24 h then the precipitate collected by filtration, washing with dioxane. The resulting solid was partitioned between EtOAc and H2O and the aqueous layer basified to pH 11 with NH4OH. The aqueous phase was neutralised to pH 7 with HCl then loaded onto an Isolute® SCX-2 cartridge which was washed with H2O and MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (C18, MeOH:H2O, 30-95%) then loaded onto an Isolute® SCX-2 cartridge which was washed with H2O and MeOH and the product eluted with 2M NH3/MeOH affording 812 (69 mg, 17%). LCMS (method I): RT 2.16 min, [M+H]+ 517.3. 1H NMR (DMSO, 400 MHz): δ 7.95-7.94 (1 H, m), 7.73 (1 H, s), 7.63-7.62 (1 H, m), 7.25-7.22 (2 H, m), 4.24 (4 H, brd s), 3.79-3.74 (6 H, m), 3.46 (2 H, s), 3.23 (3 H, q, J=7.46 Hz), 3.16-3.04 (5 H, m), 2.84 (2 H, s), 2.45-2.44 (2 H, m), 1.31 (3 H, t, J=7.45 Hz)

Provenance & Evidence