1,2-Diaminocyclohexane, trans- → 2-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester

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Reaction Steps

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 50 mg, 0.28216 mmol) was reacted with 2-bromo-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester (90 mg, 0.28216 mmol), 1,4-dioxane (20 mL), copper iodide (5.3 mg, 0.0282 mmol), trans-1,2-diamino cyclohexane (9.69 mg, 0.08464 mmol) and potassium phosphate (179.6 mg, 0.84650 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 70 mg of 2[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester (60% yield).

Provenance & Evidence