Diisopropylethylamine → N-(4-Chlorobenzyl)-2-{[(2-hydroxy-2-pyridin-3-ylethyl)(methyl)amino]methyl}-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

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Reaction Conditions

Reaction Steps

A mixture of 111 mg of N-(4-chlorobenzyl)-2-(chloromethyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide, 54 mg of 2-(methylamino)-1-pyridin-3-ylethanol (Arch. Pharm. (1961), 294, 453), and 62 μL of diisopropylethylamine in 1.5 mL of DMF is heated at 50° C. for 18 h, then cooled and partitioned between EtOAc and water. The organic phase is washed with two additional portions of water and brine, dried (Na2SO4), and concentrated under reduced pressure. Flash chromatography of the residue on silica using 5% MeOH in CH2Cl2 affords 128 mg of the title compound as a white foam. Recrystallization of a sample from EtOAc provides white crystals.

Provenance & Evidence