(E)-3-(4-chlorophenyl)prop-2-enoyl chloride

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

Procedure: To a solution of the product of Step D (91 mg, 0.4 mmol) in 2 mL HOAc was added the product of Step E (64 mg, 0.32 mmol). The resulting mixture was stirred at r.t. for 3 h then diluted with 3 mL ether. The resulting mixture was filtered and the resulting solids were washed with ether. The solids were dried under vacuum to afford the product, MS: m/z 392 (MH+), as an off-white solid. Using the appropriate starting materials and following procedures similar to those described above for Example 1, the following compounds were prepared from the corresponding quinoline-2,6-diamine intermediates: The resulting mixture was filtered the resulting solids were washed with ether The solids were dried under vacuum to afford the product, MS

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

Procedure: To a solution of (2E)-3-(4-chlorophenyl)prop-2-enoic acid (2.0 g, 11 mmol) in 50 mL methylene chloride was added oxalyl chloride (1.05 mL, 12.1 mmol) and N,N-dimethylformamide (0.05 mL, 0.6 mmol). The resulting mixture was stirred at r.t. for 6 h. The solvent was removed under vacuum. The resulting solid was diluted with hexanes and the solvent removed under vacuum to provide an off-white solid which was used without further purification. The solvent was removed under vacuum The resulting solid was diluted with hexanes the solvent removed under vacuum to provide an off-white solid which was used without further purification

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

Procedure: To a solution of the product of Step D (91 mg, 0.4 mmol) in 2 mL HOAc was added the product of Step E (64 mg, 0.32 mmol). The resulting mixture was stirred at r.t. for 3 h then diluted with 3 mL ether. The resulting mixture was filtered and the resulting solids were washed with ether. The solids were dried under vacuum to afford the product, MS: m/z 392 (MH+), as an off-white solid. Using the appropriate starting materials and following procedures similar to those described above for Example 1, the following compounds were prepared from the corresponding quinoline-2,6-diamine intermediates: The resulting mixture was filtered the resulting solids were washed with ether The solids were dried under vacuum to afford the product, MS

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

Procedure: To a solution of (2E)-3-(4-chlorophenyl)prop-2-enoic acid (2.0 g, 11 mmol) in 50 mL methylene chloride was added oxalyl chloride (1.05 mL, 12.1 mmol) and N,N-dimethylformamide (0.05 mL, 0.6 mmol). The resulting mixture was stirred at r.t. for 6 h. The solvent was removed under vacuum. The resulting solid was diluted with hexanes and the solvent removed under vacuum to provide an off-white solid which was used without further purification. The solvent was removed under vacuum The resulting solid was diluted with hexanes the solvent removed under vacuum to provide an off-white solid which was used without further purification

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

Procedure: To a solution of the product of Step D (91 mg, 0.4 mmol) in 2 mL HOAc was added the product of Step E (64 mg, 0.32 mmol). The resulting mixture was stirred at r.t. for 3 h then diluted with 3 mL ether. The resulting mixture was filtered and the resulting solids were washed with ether. The solids were dried under vacuum to afford the product, MS: m/z 392 (MH+), as an off-white solid. Using the appropriate starting materials and following procedures similar to those described above for Example 1, the following compounds were prepared from the corresponding quinoline-2,6-diamine intermediates: The resulting mixture was filtered the resulting solids were washed with ether The solids were dried under vacuum to afford the product, MS

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

Procedure: To a solution of (2E)-3-(4-chlorophenyl)prop-2-enoic acid (2.0 g, 11 mmol) in 50 mL methylene chloride was added oxalyl chloride (1.05 mL, 12.1 mmol) and N,N-dimethylformamide (0.05 mL, 0.6 mmol). The resulting mixture was stirred at r.t. for 6 h. The solvent was removed under vacuum. The resulting solid was diluted with hexanes and the solvent removed under vacuum to provide an off-white solid which was used without further purification. The solvent was removed under vacuum The resulting solid was diluted with hexanes the solvent removed under vacuum to provide an off-white solid which was used without further purification