Sodium Hydroxide → HCID 22574302, compound

Participants

Reaction Steps

A solution of 144 mg of N-(4-chlorobenzyl)-2-{[(2-hydroxy-2-pyrazin-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 3 h, then diluted with CHCl3 and added to stirred aq. NaHCO3. The aqueous phase is adjusted to pH 10-11 with added NaOH, then extracted with 6 portions of CHCl3. The combined organic phase is dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica gel (compound pre-loaded onto silica gel using CHCl3-MeOH) using 5-8% MeOH in CH2Cl2 provides 114 mg of the title compound as a white solid. Trituration with boiling acetonitrile affords white solid.

Provenance & Evidence