2,5-diazabicyclo[2.2.2]octane;dihydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is prepared according to the same procedure as described for Intermediate 7 using 2,5-diazabicyclo[2.2.2]octane dihydrochloride (J. Heterocycl. Chem, 1974, 11, 449-451). This compound is prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is prepared according to the same procedure as described for Intermediate 7 using 2,5-diazabicyclo[2.2.2]octane dihydrochloride (J. Heterocycl. Chem, 1974, 11, 449-451). This compound is prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.56 g (2.0 mmol) of 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 0.41 g (2.2 mmol) of 2,5-diazabicyclo[2.2.2]octane dihydrochloride, 0.90 ml (6.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 25 ml of acetonitrile was heated under reflux for 18 hours. The solution was evaporated to dryness and the residue was triturated with methanol and filtered to give 0.20 g of the title compound, 260°-265° C. under reflux for 18 hours The solution was evaporated to dryness the residue was triturated with methanol filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.54 g (2.0 mmole) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 0.46 g (2.5 mmole) of 2,5-diazabicyclo[2.2.2]octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 1.05 ml (7.0 mmole) of 1,8-diazabicyclo (5.4.0) undec-7-ene, and 30 ml of acetonitrile was stirred at room temperature for 23 hours. The reaction mixture was filtered and the solid was washed with acetonitrile to give 0.63 g of the title compound, mp 250°-253°. The reaction mixture was filtered the solid was washed with acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.28 g (1 mmole) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.2 g (1.1 mmole) 2,5-diazabicyclo[2.2.2]octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 0.45 ml (3.0 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 10 ml of acetonitrile was heated at reflux for four hours. After cooling to room temperature, the reaction mixture was filtered and the solid washed with ethanol and dried to give 0.27 g of the title compound, mp 275°-280° C. at reflux for four hours the reaction mixture was filtered the solid washed with ethanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.81 g (3.0 mmole) of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.74 g (4.0 mmole) of 2,5-diazabicyclo[2.2.2]octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 1.65 ml (11 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 40 ml of acetonitrile was stirred at room temperature for 25 hours and heated under reflux for two hours. The reaction mixture was filtered and the solid was washed with methanol to give 0.68 g of the title compound, mp 255°-257°. heated under reflux for two hours The reaction mixture was filtered the solid was washed with methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.52 g (2.0 mmole) of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.37 g (2.0 mmole) of 2,5-diazabicyclo(2.2.2)octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 0.90 ml (6.0 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 25 ml of acetonitrile was heated under reflux for 21 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was recrystallized from ethanol to give 0.30 g of the title compound, mp 270°-272°. under reflux for 21 hours The reaction mixture was filtered the filtrate was evaporated to dryness The residue was recrystallized from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound is prepared according to the same procedure as described for Intermediate 7 using 2,5-diazabicyclo[2.2.2]octane dihydrochloride (J. Heterocycl. Chem, 1974, 11, 449-451). This compound is prepared