cyclohexanecarbohydrazide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.48 gm (0.04 mole) of 4-acetylpyridine 1-oxide, 5.68 gm (0.04 mole) of cyclohexanecarboxylic acid hydrazide and 100 ml of absolute ethanol is refluxed 4 hours. The reaction mixture is concentrated in vacuo to dryness to give a solid. The solid is crystallized from isopropanol to furnish 8.20 gm (79%) of the title compound; mp 245.3°. is refluxed 4 hours The reaction mixture is concentrated in vacuo to dryness to give a solid The solid is crystallized from isopropanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.48 gm (0.04 mole) of 4-acetylpyridine 1-oxide, 5.68 gm (0.04 mole) of cyclohexanecarboxylic acid hydrazide and 100 ml of absolute ethanol is refluxed 4 hours. The reaction mixture is concentrated in vacuo to dryness to give a solid. The solid is crystallized from isopropanol to furnish 8.20 gm (79%) of the title compound; mp 245.3°. is refluxed 4 hours The reaction mixture is concentrated in vacuo to dryness to give a solid The solid is crystallized from isopropanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4.26 gm (0.03 mole) of cyclohexanecarboxylic acid hydrazide, 3.63 gm (0.03 mole) of 4-acetylpyridine and 100 ml of ethanol is refluxed 7 hr. The solvent is evaporated in vacuo to give a white solid. The product is crystallized from ethyl acetate to yield 5.38 gm (73%) of the title compound having a melting point of 195.3° C. The solvent is evaporated in vacuo to give a white solid The product is crystallized from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 28 Grams of methyl cyclohexylcarboxylate and 15 g of 85%-NH2NH2.H2O were dissolved in 50 ml of isopropyl alcohol, and the solution was refluxed by heating for 10 hours. The reaction mixture was concentrated, and the crystals precipitated by adding water were collected by filtration, then the crystals were washed with water, then recrystallized from water to yield 20 g of cyclohexanecarbohydrazide in the form of colorless needle-like crystals. the solution was refluxed by heating for 10 hours The reaction mixture was concentrated the crystals precipitated by adding water were collected by filtration the crystals were washed with water recrystallized from water

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl cyclohexane carboxylate (12 g, 83.9 mmol) in MeOH (50 mL) was added hydrazine (5.3 mL, 1.67 mol). The reaction mixture was heated at 65° C. overnight. The reaction mixture was cooled to room temperature and the resultant solid was collected by filtration and was dried in vacuo to give 4.0 g of cyclohexanecarboxylic acid hydrazide. The reaction mixture was cooled to room temperature the resultant solid was collected by filtration was dried in vacuo

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl cyclohexane carboxylate (12 g, 83.9 mmol) in MeOH (50 mL) was added hydrazine (5.3 mL, 1.67 mol). The reaction mixture was heated at 65° C. overnight. The reaction mixture was cooled to room temperature and the resultant solid was collected by filtration and was dried in vacuo to give 4.0 g of cyclohexanecarboxylic acid hydrazide. The reaction mixture was cooled to room temperature the resultant solid was collected by filtration was dried in vacuo

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-ethoxy-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Preparation 3(A) (5 g, 24.5 mmol) in glacial acetic acid (75 mL) was added cyclohexanecarboxylic acid hydrazide (Preparation 14) (3.5 g, 24.5 mmol). The reaction was heated at 120° C. for 2.5 hours, was cooled to room temperature, and EtOAc (50 mL), water (50 mL) and aqueous NaHCO3 (50 mL) were added. The mixture was stirred for 5 minutes and Et2O was added (125 mL). The suspension was stirred for 15 minutes and the solids were removed by filtration with the aid of Et2O to provide 5.92 g of 1-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one. was cooled to room temperature The suspension was stirred for 15 minutes the solids were removed by filtration with the aid of Et2O

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of methyl cyclohexane carboxylate (12 g, 83.9 mmol) in MeOH (50 mL) was added hydrazine (5.3 mL, 1.67 mol). The reaction mixture was heated at 65° C. overnight. The reaction mixture was cooled to room temperature and the resultant solid was collected by filtration and was dried in vacuo to give 4.0 g of cyclohexanecarboxylic acid hydrazide. The reaction mixture was cooled to room temperature the resultant solid was collected by filtration was dried in vacuo

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-ethoxy-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Preparation 3(A) (5 g, 24.5 mmol) in glacial acetic acid (75 mL) was added cyclohexanecarboxylic acid hydrazide (Preparation 14) (3.5 g, 24.5 mmol). The reaction was heated at 120° C. for 2.5 hours, was cooled to room temperature, and EtOAc (50 mL), water (50 mL) and aqueous NaHCO3 (50 mL) were added. The mixture was stirred for 5 minutes and Et2O was added (125 mL). The suspension was stirred for 15 minutes and the solids were removed by filtration with the aid of Et2O to provide 5.92 g of 1-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one. 1H NMR (CDCl3) δ 8.36 (s, NH), 7.50 (m, 1H), 7.41 (m, 2H), 7.30 (d, 1H), 4.13 (d, 1H), 3.47 (d, 1H), 2.87 (m, 1H), 2.24 (d, 1H), 2.00 (m, 2H), 1.72-1.51 (m, 4H), 1.33 (m, 2H), 1.16 (m, 1H); MS 283.4 (M+1), 281.3 (M−1). was cooled to room temperature The suspension was stirred for 15 minutes the solids were removed by filtration with the aid of Et2O

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acid (0.920 mg; 3.45 mmol) in chloroform (50 mL) was added thionyl chloride (2.51 mL; 34.50 mmol) and the mixture was stirred at 80° C. for 3 h and was then evaporated to dryness. The resulting 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetyl chloride (0.480 g; 1.68 mmol) was dissolved in dichloromethane (12 mL) and a mixture of triethylamine (0.945 mL; 6.73 mmol) and cyclohexanecarboxylic acid hydrazide (0.232 g; 1.60 mmol) in dichloromethane (8 mL) was added at 0° C. The mixture was stirred at room temperature for 2 h and p-toluenesulfonyl chloride (0.324 g, 1.68 mmol) was added. The resulting mixture was stirred overnight at room temperature, diluted with dichloromethane, washed with an aqueous solution of sodium carbonate, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluent: 12 to 100% ethyl acetate in heptane) to give 0.0088 g (1.40%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-cyclohexyl-1,3,4-oxadiazole-2-carboxamide as a white solid. was then evaporated to dryness was added at 0° C The mixture was stirred at room temperature for 2 h The resulting mixture was stirred overnight at room temperature washed with an aqueous solution of sodium carbonate concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (eluent: 12 to 100% ethyl acetate in heptane)

反応条件: temp:0.00; pressure:0.00; stir: