(3-chlorophenyl)hydrazine

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: This compound was prepared by the same methodology described for EXAMPLE 1 with 3-chlorophenyl hydrazine.HCl substituted for phenyl hydrazine. There was obtained the title compound; HRMS (M+H)+: calc. 467.094465; found 467.091517. This compound was prepared by the same methodology

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

Procedure: A mixture of 3.12 g 2-aminoacetophenone and 3.29 g 3-chlorophenylhydrazine in 4 ml HOAc and 20 ml EtOH was refluxed for one hour. The cooled reaction mixture was diluted with water and the precipitate was collected, washed with water, and dried to give 5.16 g solid. Recrystallization from methanol gave 2.12 g solid, m.p. 131°-134° C. was refluxed for one hour The cooled reaction mixture the precipitate was collected washed with water dried

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

Procedure: A mixture of 3.12 g 2-aminoacetophenone and 3.29 g 3-chlorophenylhydrazine in 4 ml HOAc and 20 ml EtOH was refluxed for one hour. The cooled reaction mixture was diluted with water and the precipitate was collected, washed with water, and dried to give 5.16 g solid. Recrystallization from methanol gave 2.12 g solid, m.p. 131°-134° C. was refluxed for one hour The cooled reaction mixture the precipitate was collected washed with water dried

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

Procedure: A mixture of 3.12 g 2-aminoacetophenone and 3.29 g 3-chlorophenylhydrazine in 4 ml HOAc and 20 ml EtOH was refluxed for one hour. The cooled reaction mixture was diluted with water and the precipitate was collected, washed with water, and dried to give 5.16 g solid. Recrystallization from methanol gave 2.12 g solid, m.p. 131°-134° C. was refluxed for one hour The cooled reaction mixture the precipitate was collected washed with water dried

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

Procedure: 2-(3-Chloro-phenyl)-3-phenyl-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. The desired compound (53.9 mg) was prepared from 142.7 mg of 2-(3-chloro-phenyl)-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (made as in Example 176, Steps A and B) replacing phenylhydrazine with (3-chloro-phenyl)-hydrazine, as described in Example 43, Step D, using 102.1 mg of phenylboronic acid. MS (ESI): exact mass calculated for C24H26ClN3O2, 423.17; found, m/z 424.1 [M+H]+.

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

Procedure: This compound was prepared by the same methodology described for EXAMPLE 1 with 3-chlorophenyl hydrazine · HCl substituted for phenyl hydrazine. There was obtained the title compound; HRMS (M+H)+ : calc. 467.094465; found 467.091517. This compound was prepared by the same methodology

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

Procedure: 2-(3-Chloro-phenyl)-3-phenyl-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. The desired compound (53.9 mg) was prepared from 142.7 mg of 2-(3-chloro-phenyl)-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (made as in Example 176, Steps A and B) replacing phenylhydrazine with (3-chloro-phenyl)-hydrazine, as described in Example 43, Step D, using 102.1 mg of phenylboronic acid. MS (ESI): exact mass calculated for C24H26ClN3O2, 423.17. found, m/z 424.1 [M+H]+.

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

Procedure: 2-(3-Chloro-phenyl)-3-phenyl-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. The desired compound (53.9 mg) was prepared from 142.7 mg of 2-(3-chloro-phenyl)-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (made as in Example 176, Steps A and B) replacing phenylhydrazine with (3-chloro-phenyl)-hydrazine, as described in Example 43, Step D, using 102.1 mg of phenylboronic acid. MS (ESI): exact mass calculated for C24H26ClN3O2, 423.17. found, m/z 424.1 [M+H]+.

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

Procedure: A 0.6 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 14.76 g. of m-chlorophenylhydrazine is added followed in 5 minutes by 12.92 g. of cinnamonitrile. The reaction mixture is refluxed for 6 hours, then cooled in an ice-bath. The precipitate formed is collected by filtration, then is dissolved in dichloromethane. This solution is passed through a short column of a hydrous magnesium silicate. The effluent is heated to reflux on a steam bath and hexane is added until a precipitate occurs. The product is collected, then is recrystallized from dichloromethane-hexane to give 7.55 g. of the product of the Example as salmon colored needles, m.p. 164°-165° C. The reaction mixture is refluxed for 6 hours cooled in an ice-bath The precipitate formed is collected by filtration is dissolved in dichloromethane The effluent is heated to reflux on a steam bath hexane is added until a precipitate The product is collected is recrystallized from dichloromethane-hexane to give 7.55 g

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

Procedure: This compound was prepared by the same methodology described for EXAMPLE 1 with 3-chlorophenyl hydrazine.HCl substituted for phenyl hydrazine. There was obtained the title compound; HRMS (M+H)+: calc. 467.094465; found 467.091517. This compound was prepared by the same methodology

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

Procedure: This compound was prepared by the same methodology described for EXAMPLE 1 with 3-chlorophenyl hydrazine.HCl substituted for phenyl hydrazine. There was obtained the title compound; HRMS (M+H)+: calc. 467.094465; found 467.091517. This compound was prepared by the same methodology