Pyridine → HCID 69192953, compound

Participants

Reaction Steps

To a solution of the product from Step A above in 6 mL of 3:2:1 tetrahydrofuran/methanol/water was added lithium hydroxide monohydrate (0.23 g, 5.58 mmol). The mixture was allowed to stir overnight and the volatiles were removed under reduced pressure. Additional water was added, and the solution was acidified with citric acid monohydrate. The resultant precipitate was collected, washed with water, and dried in vacuo. To an ice-cold solution of this intermediate (1.0 g, 3.6 mmol) in 32 mL of pyridine was added methanesulfonyl chloride (0.41 g, 3.6 mmol) dropwise, and the resultant mixture was allowed to stir for one hour. Dry ammonia gas was bubbled into the reaction mixture for 2 minutes. The excess ammonia was then removed under reduced pressure, and the solution was cooled again in ice and treated with methanesulfonyl chloride (3.43 g, 30.0 mmol). The resultant mixture was allowed to warm to room temperature overnight. The reaction was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. The product was extracted with ethyl acetate, and the combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The resultant crystalline solid was triturated with ether, and the precipitate was collected to afford the title compound as a light orange powder.

Provenance & Evidence