The condensation of 2-nitrophenyl isocyanate (V) with endo-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (IV) in THF/cyclohexane gives the corresponding 2-nitrophenylurea (VI), which is reduced with H2 over Pd/C in ethanol to yield the 2-aminophenylurea (VII). The acylation of (VII) with phenyl chloroformate (VIII) in toluene affords the carbamate (IX), which is finally cyclized by means of NaOH in ethanol.
This compound has been obtained by two different ways: 1. The reaction of 2,3-dihydro-1H-benzimidazol-2-one (I) with trichloromethyl chloroformate (II) in THF gives 2-oxo-2,3-dihydro-1H-benzimidazol-2-ylcarbonyl chloride (III), which is condensed with endo-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (IV) in THF, yielding the corresponding amide (V). Finally, this compound is alkylated with ethyl chloride (VI) and NaH in DMF. 2. The condensation of 2-nitrophenyl isocyanate (VII) with endo-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (IV) in THF/cyclohexane gives the corresponding 2-nitrophenylurea (VIII), which is reduced with H2 over Pd/C in ethanol to yield the 2-aminophenylurea (IX). The acylation of (IX) with phenyl chloroformate (X) in toluene affords the carbamate (XI), which is cyclized by means of NaOH in ethanol to afford the amide (V). Finally, this compound is alkylated with ethyl chloride (VI) and NaH in DMF.
The condensation of 2-nitrophenyl isocyanate (VII) with endo-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (IV) in THF/cyclohexane gives the corresponding 2-nitrophenylurea (VIII), which is reduced with H2 over Pd/C in ethanol to yield the 2-aminophenylurea (IX). The acylation of (IX) with phenyl chloroformate (X) in toluene affords the carbamate (XI), which is cyclized by means of NaOH in ethanol to afford the amide (V). Finally, this compound is alkylated with ethyl chloride (VI) and NaH in DMF.
The reaction of 2,3-dihydro-1H-benzimidazol-2-one (I) with trichloromethyl chloroformate (II) in THF gives 2-oxo-2,3-dihydro-1H-benzimidazol-2-ylcarbonyl chloride (III), which is condensed with endo-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (IV) in THF, yielding the corresponding amide (V). Finally, this compound is alkylated with isopropyl bromide (VI) and NaH in DMF.
The condensation of 2-nitrophenyl isocyanate (VII) with endo-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (IV) in THF/cyclohexane gives the corresponding 2-nitrophenylurea (VIII), which is reduced with H2 over Pd/C in ethanol to yield the 2-aminophenylurea (IX). The acylation of (IX) with phenyl chloroformate (X) in toluene affords the carbamate (XI), which is cyclized by means of NaOH in ethanol to afford the amide (V). Finally, this compound is alkylated with isopropyl bromide (VI) and NaH in DMF.
The esterification of endo-8-methyl-8-azabicyclo[3,2,1]octan-3-ol (I) with trichloromethyl chloroformate (II) in acetonitrile gives the corresponding chloroformate (III), which is condensed with 5-methoxy-2-nitroaniline (IV) in pyridine, yielding the carbamate (V). The hydrogenation of the nitro group of (V) with H2 over Pd/C in methanol affords the expected amino derivative (VI). Finally, this compound is cyclized with trichloromethyl chloroformate (II) and Et3N in THF.
The reaction of 2,3-dihydro-1H-benzimidazol-2-one (I) with trichloromethyl chloroformate (II) in THF gives 2-oxo-2,3-dihydro-1H-benzimidazol-2-ylcarbonyl chloride (III), which is then condensed with endo-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (IV) in THF.