Sodium Iodide → HCID 57420754, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-pyrimidin-5-yl-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (108 mg, 0.34 mmol) in EtOAc (5.0 ml) is added HCl-dioxane solution (4.0N, 2.0 ml). The resulting mixture is stirred at 50° C. overnight, and then organic solvents are evaporated. To the residue are added acetonitrile (5.0 ml), 2-chloro-(4-cyclobutyl-piperazine)-acetamide (74 mg, 0.34 mmol, 1.0 eq.), K2CO3 (94 mg, 0.68 mmol, 2.0 eq.), and NaI (30 mg). The resulting mixture is stirred at 40° C. overnight. Water (10.0 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by preparative silica gel flash chromatography (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 9.08 (1H, s), 8.87 (2H, s), 7.04 (1H, s), 3.60˜3.65 (6H, m), 3.41 (2H, s), 3.09 (2H, t), 2.91 (4H, m), 2.70 (1H, m), 2.30 (4H, m), 1.66˜2.08 (6H); MS (+VE) m/z 398.2 (M++1).

Provenance & Evidence