(2-methylphenyl)hydrazine

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

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

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

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

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

Conditions: temp:92.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl-8-chloro-1-[4-(1H-pyrazol-1-yl)benzyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate (48 mg, 0.113 mmol), potassium carbonate (78 mg, 0.56 mmol, 5 equiv), and 2-methylphenyl hydrazine (23 mg, 0.19 mmol, 1.7 equiv) were combined in 1,2-dimethoxyethane (2 mL) and heated to 92° C. for 2 hours. The mixture was cooled to ambient temperature, diluted with water (20 mL) and extracted with ethyl acetate (3×40 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 94:6; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.24 (1H, d, J=7.2 Hz), 7.88 (1H, s), 7.71-7.61 (4H, m), 7.47-7.42 (3H, m), 7.37-7.30 (3H, m), 7.29 (1H, s), 6.4 (1H, m), 6.34 (2H, s), 2.36 (3H, s), ppm; high resolution mass spectrometry (ES+) m/z 467.1388 [(M+H)+; calculated for C26H20ClN6O: 467.1382]. The mixture was cooled to ambient temperature extracted with ethyl acetate (3×40 mL) The combined organic extracts were dried with sodium sulfate filtered concentrated in vacuo The residue was purified by silica gel chromatography (100:0 to 94:6; chloroform:methanol)

Conditions: temp:92.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl-8-chloro-1-[4-(1H-pyrazol-1-yl)benzyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate (48 mg, 0.113 mmol), potassium carbonate (78 mg, 0.56 mmol, 5 equiv), and 2-methylphenyl hydrazine (23 mg, 0.19 mmol, 1.7 equiv) were combined in 1,2-dimethoxyethane (2 mL) and heated to 92° C. for 2 hours. The mixture was cooled to ambient temperature, diluted with water (20 mL) and extracted with ethyl acetate (3×40 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 94:6; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.24 (1H, d, J=7.2 Hz), 7.88 (1H, s), 7.71-7.61 (4H, m), 7.47-7.42 (3H, m), 7.37-7.30 (3H, m), 7.29 (1H, s), 6.4 (1H, m), 6.34 (2H, s), 2.36 (3H, s), ppm; high resolution mass spectrometry (ES+) m/z 467.1388 [(M+H)+; calculated for C26H20ClN6O: 467.1382]. The mixture was cooled to ambient temperature extracted with ethyl acetate (3×40 mL) The combined organic extracts were dried with sodium sulfate filtered concentrated in vacuo The residue was purified by silica gel chromatography (100:0 to 94:6; chloroform:methanol)

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

Procedure: The title compound was prepared from 1-ethyl-4-(5-hexenyl)-2-oxocyclohexaneacetic acid methyl ester (isomer A) and 2-methylphenylhydrazine as described in Example 1, m.p. 110°-111° C.

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

Procedure: The title compound was prepared from 1-ethyl-4-(5-hexenyl)-2-oxocyclohexaneacetic acid methyl ester (isomer B) and 2methylphenylhydrazine as described in Example 1, m.p. 111°-112° C.

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

Procedure: The title compound was prepared from 1-ethyl-4-(5-hexenyl)-2-oxocyclohexaneacetic acid methyl ester (isomer B) and 2methylphenylhydrazine as described in Example 1, m.p. 111°-112° C.

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

Procedure: The title compound was prepared from 1-ethyl-4-(5-hexenyl)-2-oxocyclohexaneacetic acid methyl ester (isomer A) and 2-methylphenylhydrazine as described in Example 1, m.p. 110°-111° C.

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

Procedure: The title compound was prepared from 1-ethyl-4-(5-hexenyl)-2-oxocyclohexaneacetic acid methyl ester (isomer B) and 2-methylphenylhydrazine as described in Example 1, m.p. 111°-112° C.