To a suspension of rac-4-benzyl-2-morpholinecarboxylic acid hydrochloride (77 mg, 0.30 mmol) in THF (2 ml) was added DMF (2.0 μl, 0.025 mmol) followed by oxalyl chloride (36 ul, 0.41 mmol). After stirring at room temperature for 20 min. the mixture was evaporated to dryness and then re-suspended in THF (2 ml). A solution of 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (60 mg, 0.2 mmol) and diisopropylethylamine (110 μl, 0.9 mmol) in THF (1 ml) was then added and the reaction stirred for at room temperature for 1 h. After 1 h, MeOH (1 ml) was added, the mixture concentrated and the residue purified through preparative LC/MS to give N-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-rac-4-benzyl-2-morpholinecarboxamide (AT8769) as a white solid (10 mg, 9%). (LC/MS (basic method): Rt 2.86 min, [M+H]+ 463).
