Diisopropylethylamine → N-(4-fluorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyrazin-2-ylethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

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A mixture of N-(4-fluorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (104 mg, 0.275 mmol), (1R)-2-(methylamino)-1-pyrazin-2-ylethanol (Preparation 80, 65 mg, 0.0.42 mmol) and diisopropylethylamine (72 μL, 0.0.41 mmol) in dry DMF (5.5 mL) was stirred at room temperature for 17 hours. The solution was then diluted with water (20 mL). The resulting precipitate was collected by filtration and the collected solid was dried in vacuo, providing a white solid. Attempted recrystallization from acetonitrile (20 mL, dissolved with warming and then cooled to room temperature) gave the title compound (31 mg) as a white solid upon concentrating the filtrate.

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