4-Pyridinecarboxylic acid, 1-oxide → HCID 131717533, compound

Participants

Reaction Steps

To a mixture of 20 g of 8-chloro-11-(4-piperidylidene)-6,11-dihydro-3-methyl-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (product from Preparative Example 7, Step E), 1.39 g of isonicotinic acid N-oxide, and 1.35 g of 1-hydroxybenzotriazole in 60 mL CH2Cl2 at 0° C. was added 1.91 g of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (DEC). The reaction mixture was slowly allowed to warm to room temperature overnight. The reaction mixture was quenched with water, basified with 10% NaOH, and extracted with CH2Cl2. The combined organic portions were washed with brine, dried over Na2SO4, and concentrated in vacuo. The product was flash chromatographed using 5% methanol in methylene chloride to give 2.52 g of a product which could be triturated with CH2Cl2 /diisopropylether (1:20 parts by volume) to give the title compound as a white solid.

Provenance & Evidence