Sodium hydride → HCID 13785478, compound

Participants

Reaction Steps

To a suspension of N,N-dimethyl 2-[N-(2-dimethylaminoethyl)aminosulfonyl]-6-nitrobenzamide hydrochloride (347 mg, 0.91 mmol) in DMF (5 ml) under N2 was added 50% NaH (87 mg, 1.82 mmol). After stirring at 20°-25° for 15 minutes until all of the NaH had reacted, a solution of 2-(2-bromoethoxy)tetrahydro-2H-pyran in DMF (2 ml) was added. The solution was stirred at 20°-25° under N2 for 20 hours and then concentrated under reduced pressure to remove most of the DMF. The residue was partitioned between EtOAc and a saturated aqueous solution of NaCl. After drying (Na2SO4) the EtOAc extract, filtering and concentrating, the residue was chromatographed over silica gel. Elution with 7% MeoH-93% CHCl3 gave 100 mg of product.

Provenance & Evidence