(-)-(2S)-Tifluadom Hydrochloride and Two of its (-)-(2S)-2-(Acylaminomethyl)benzodiazepine Hydrochloride Analogues

The structures of three (-)-(2S)-(acylaminomethyl)benzodiazepine hydrochlorides, namely, 5-(2-fluorophenyl)-1-methyl-2-(3-thenoylaminomethyl)-2,3-dihydro-1H-1,4-benzodiazepin-4-ium chloride [C₂₂H₂₁FN₃OS⁺.Cl^-, (1), tifluadom], 1,7-dimethyl-5-phenyl-2-(3-thenoylaminomethyl)-2,3-dihydro- 1H-1,4-benzodiazepin-4-ium chloride [C₂₃H₂₄N₃OS⁺.Cl^-, (2)] and 5-(4-fluorophenyl)-1,8-dimethyl-2-(p-toluoylaminomethyl)-2,3-dihydro-1H-1,4-benzodiazepin-4-ium chloride hemi(isobutyl methyl ketone) solvate [C₂₆H₂₇FN₃O⁺.Cl^-.0.5C₆H₁₂O, (3)] are reported. The conformations of the molecules are very similar. The seven-membered ring has a conformation halfway between a distorted boat and a distorted sofa, with the 2-substituent in a flagpole orientation and the acylaminomethyl moiety in an extended conformation.

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