Pyridine → HCID 19957044, compound

Participants

Reaction Steps

To a cooled mixture of the diamine dihydrochloride of Example 378 (b) (1.16 g, 28 mmol), CH2Cl2 (25 mL) and pyridine (6 mL) under nitrogen was added methanesulfonyl chloride (0.64 g, 56 mmol). The reaction mixture was stirred, with cooling in ice-bath, for 13/4 hours and then was poured into a solution of water/saturated Na2CO3. The layers were separated, the aqueous layer was extracted with CH2Cl2, and the organic layers were combined and washed with water/saturated Na2CO3. The organic layer was dried over Na2SO4, the solvent was removed in vacuo, and the residue was diluted with hexane. A precipitate formed which was slurried with t-BuOMe and collected by filtration. The solid was recrystallized from hot CH2Cl2 /hexane to afford 0.85 g (73%) of 4,5-dihydro-4-methyl-1-phenyl-3-[1-(4-methylsulfonylaminophenyl)methyl]-1H-2,4-benzodiazepine as an off-white solid, m.p. 182°-185° C.

Provenance & Evidence