Pyridine → HCID 19957031, compound

Participants

Reaction Steps

To an ice-cooled solution of the amine of Example 384 (b) (3.33 g, 7.3 mmol) in CH2Cl2 (35 mL) was added pyridine (17 mL), followed by methanesulfonyl chloride (0.84 mL) in CH2Cl2 (10 mL). The mixture was warmed to room temperature, stirred for 1.5 hours, and poured into saturated K2CO3 (50 mL). The organic layer was separated and the precipitate which formed over 2 hours was collected by filtration. The solid was converted into the fumarate salt, which was purified by column chromatography on neutral alumina eluting with 5-6% methanol in CH2Cl2. The purified salt was then converted back into the free base and then into the hydrochloride salt to afford 1.224 g of 4,5-dihydro-4-methyl-1-(4-methoxyphenyl)-3-[2-(4-methylsulfonylaminophenyl)ethyl]-1H-2,4-benzodiazepine hydrochloride as a light yellow powder, m.p. 149° C. (dec.).

Provenance & Evidence