Chloride → HCID 136395935, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-cyclohexyl-N-(2,3-dihydro-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-3-yl)propanamide (162 mg, 0.4 mmol), 2-aminoethanol (96 μL, 98 mg, 1.6 mmol) and mereuric chloride (141 mg, 0.52 mmol) in THF (5 mL) was stirred at 55° C. for 1 h. The solvent was evaporated under reduced pressure and the residue was triturated with EtOAc/Hexane. The solid was collected and dried in vacuo to give 3-cyclohexyl-N-[2,3-dihydro-2-(2-hydroxyethylimino)-5-phenyl-1H-1,4-benzodiazepin-3-yl)propanamide as a solid (120 mg, 69%). A sample (90 mg, 0.2 mmol) was dissolved in dichloromethane (7 mL), cooled to 0° C. and methanesulfonyl chloride (19 μL, 28 mg, 2.4 mmol) and diisopropylethylamine (75 μl, 56 mg, 0.43 mmol) were added. The mixture was stirred at 0° C. for 30 min., then at room temperature for 2 h. The solvent was evaporated under reduced pressure, toluene was added and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH (98:2) to give 3-cyclohexyl-N-{2,4-dihydro-6-phenyl-1H-imidazo[1,2-a][1,4]benzodiazepin-4-yl}propanamide as a solid (40 mg, 48%), m.p. 202°-208.5° C.

Provenance & Evidence