Cesium carbonate → HCID 59605634, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-1-[4-(2-hydroxy-1,1-dimethylethyl)piperazin-1-yl]ethanone (65 mg, 0.14 mmol), 2-ethylbenzimidazole (23 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium (4 mg, 2.5 mol %), XPhos (7 mg, 10 mol %) and Cs2CO3 (70 mg, 0.21 mmol) in dioxane (2 mL) was purged with argon then heated at 110° C. for 24 h in a sealed tube. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH/DCM. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) followed by reverse phase HPLC (Phenomenex Gemini 5 μm C18, 20 nM NEt3 in water on a gradient acetonitrile 10-95%) affording 712 as a yellow solid (14 mg, 17%). LCMS (method I): RT 2.58 min, [M+H]+ 565.2. 1H NMR (CDCl3, 400 MHz): δ 8.01-7.98 (1 H, m), 7.76-7.75 (1 H, m), 7.29-7.29 (2 H, m), 4.41 (4 H, s), 4.18 (2 H, s), 3.93-3.75 (9 H, m), 3.56 (2 H, brd s), 3.34 (2 H, q, J=7.47 Hz), 2.90-2.70 (4 H, brd m), 1.43 (3 H, t, J=7.47 Hz), 1.23-1.21 (6 H, m)

Provenance & Evidence