Sodium Bicarbonate → N-(4-Chlorobenzyl)-3-(hydroxymethyl)-2-{[(2-hydroxy-2-quinolin-2-ylethyl)(methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

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A solution of 174 mg of N-(4-chlorobenzyl)-2-{[(2-hydroxy-2-quinolin-2-ylethyl)(methyl)amino]methyl}-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 3 mL of 75% TFA in CH2Cl2 is stirred at room temperature for 2.5 h, then diluted with CHCl3 and added to stirred aq. NaHCO3. The aqueous phase is extracted with 4 portions of CH2Cl2, and the combined organic phases dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica gel using 3% MeOH in CH2Cl2 provides 146 mg of the title compound as a white solid. Recrystallization from EtOAc-hexane affords white solid.

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