Potassium Carbonate → 2-Bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine

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Reaction Steps

A mixture of 2-bromo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine hydrochloride (3.03 g, 11.86 mmol), 1-(chloroacetyl)-4-cyclobutylpiperazine (2.57 g, 11.86 mmol), K2CO3 (4.91 g, 35.58 mmol) and KI (166 mg, 1 mmol) in CH3CN (20 ml) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (20 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (3×30 mL). The combined extracts are washed with brine (50 μL), dried and evaporated. The resulting oil is purified by flash column with DCM/MeOH/NH4OH (100:5:0.5) to give the title compound as a light yellow solid. MS (M+1): 398.9; 1H NMR (δ, CDCl3): 3.72 (s, 2H), 3.56-3.65 (m, 4H), 3.41 (s, 2H), 2.81-2.95 (m, 4H), 2.67-2.76 (m, 1H), 2.27-2.32 (m, 4H), 1.65-2.08 (m, 6H).

Provenance & Evidence