Certain 1-aminomethyl-6-phenyl 4h-s-triazolo(4,3-a)(1,4)benzodiazepines

Abstract

Abstract 1-(3-((1,3-DI(O=)-ISOINDOLIN-2-YL)-CH2-),5-(X-CH2-)-4H- 1,2,4-TRIAZOL-4-YL-),2-(PHENYL(B)-CO-)-BENZENE(A) WHEREIN A AND B HAVE THE SIGNIFICANCE OF ABOVE, AND WHEREIN X IS CHLORO OR BROMO; (5) TREATING B WITH AN AMINE OF THE FORMULA R''-NH-R" WHEREIN R'' IS ALALKYL DEFINED AS ABOVE, OR HYDROGEN, WHEREIN R" IS ALKYL DEFINED AS ABOVE OR TOGETHER R''-NN-R" IS PYROLIDINO, PIPERIDINO, 4-METHYL- OR 4-PHENYLPIPERAZINO, IN THE PRESENCE OF AN ALKALI IODIDE, TO GIVE THE CORRESPONDING 2-(5-((SUBSTITUTED AMINO)METHYL) -3- (PHTHALIMIDOMETHYL)-4H-1,2,4TRAZOL-4-)BENZOPHENONE VI: 1-(3-((1,3-DI(O=)-ISOINDOLIN-2-YL)-CH2-),5-(R''-N(-R")- CH2-)-4H-1,2,4-TRIAZOL-4-YL-),2-(PHENYL(B)-CO-)- BENZENE(A) WHEREIN R'', R", A AND B HAVE THE SIGNIFICANCE AS DEFINED ABOVE; AND (6) HEATING VI WITH HYDRAZINE HYDRATE TO GIVE THE COMPOUND OF FORMULA VII ABOVE. WHEREIN A AND B HAVE THE SIGNIFICANCE OF ABOVE; (4) TREATING IV WITH A HALOGENATING AGENT SELECTED FROM THIONYL CHLORIDE AND PHOSPHORUS TRIBROMIDE TO OBTAIN THE CORRESPONDING 2-(3-(PHTHALIMINOMETHYL)5-(HALOMETHYL)-4H-1,2,4- TRIAZOL - 4 - YL)BENZOPHENONE OF FORMULA V: 4H-1,2,4-TRIAZOL-4-YL-),2-(PHENYL(B)-CO-)-BENZENE(A) 1-(3-((1,3-DI(O=)-ISOINDOLIN-2-YL)-CH2-),5-(HO-CH2-)- 1-(R"-N(-R'')-CH2-),6-(PHENYL(B)-)-4H-S-TRIAZOLO(4,3-A) (1,4)BENZO(A)DIAZEPINE WHEREIN A AND B HAVE THE SIGNIFICANCE OF ABOVE; (3) TREATING III WITH FORMALDEHYDE AT 100 TO 150*C. TO OBTAIN THE CORRESPONDING 2(3-(PHTHALIMIDOMETHYL)-5-(HYDROXYMETHYL)- 4H-1,2,4-TRAZOL-4-YL)BENZOPHENONE OF THE FORMULA IV; TRIAZOL-4-YL-),2-(PHENYL(B)-CO-)-BENZENE(A) 1-(3-((1,3-DI(O=)-ISOINDOLIN-2-YL)-CH2-)-4H-1,2,4- WHEREIN A AND B HAVE THE SIGNIFICANCE OF ABOVE; (2) TREATING II WITH PHTHALIMIDE, TRIPHENYLPHOSPHINE AND DIETHYL AZODICARBOXYLATE FOR 2-36 HOURS AT BETWEEN 0-40*C. TO OBTAIN THE CORRESPONDING 2-(3(PHTHALIMIDOMETHYL)-4H-1,2,4-TRIAZOL-4-YL)BENZOPHENONE OF FORMULA III BENZENE(A) 1-(3-(HO-CH2-)-4H-1,2,4-TRIAZOL-4-YL-),2-(PHENYL(B)-CO-)- WHEREIN A AND B HAVE THE SIGNIFICANCE OF ABOVE, WITH FORMALDEHYDE TO OBTAIN THE CORRESPONDING 2-(3-(HYDROXYMETHYL)-4H-1,2,4-TRIAZOL-4-YL)BENZOPHENONE OF FORMULA II 1-(4H-1,2,4-TRIAZOL-4-YL-),2-(PHENYL(B)-CO-)-BENZENE(A) IS PYRROLIDINO, PIPERIDINO, MORPHOLINO, 4-METHYL- OR 4PHENYLPIPERAZINO; AND WHEREIN THE RINGS A AND B ARE UNSUBSTITUTED OR SUBSTITUTED BY ONE OR TWO SUBSTITUENTS SELECTED FROM THE GROUP CONSISTING OF HALOGEN, NITRO, CYANO, TRIFLUOROMETHYL, AND ALKYL, ALKOXY, ALKYLTHIO, ALKYLSULFINYL, ALKYLSULFINYL, ALKANOYLAMINO IN WHICH THE CARBON MOIETY IS OF 1 TO 3 CARBON ATOMS, INCLUSIVE, AND DIALKYLAMINO IN WHICH THE ALKYL GROUP IS DEFINED AS ABOVE, WHICH COMPRISES THE STEPS: (1) HEATING TO A TEMPERATURE OF 100-150*C. A MIXTURE OF A 2-(4H-1,2,4:TRIAZOL-4-YL)BENZOPHENONE OF THE FORMULA I 1. A PROCESS FOR THE PRODUCTION OF 1(-(SUBSTITUTED AMINO)METHYL) -6- PHENYL-4H-S-TRIAZOLOR(4,3-A)(1,4)BENZODIAZEPINES OF FORMULA VII: WHEREIN R'' IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND ALKYL OF 1 TO 3 CARBON ATOMS, INCLUSIVE, WHEREIN R" IS ALKYL AS DEFINED ABOVE, OR, TOGETHER R''-N(-R")-

Inventors

• 👤 M Gall
• 👤 J Hester

Bibliographic Details