2-cyclobutylethanamine

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100-mL round bottom flask, 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (0.64 g, 3.6 mmol), chloroform (14 mL), dimethylformamide (0.1 mL) and thionyl chloride (1.2 mL) were added. The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (13 mL) and added dropwise to the mixture of cyclobutylethylamine (0.47 g, 4.74 mmol) and triethylamine (0.8 mL) in dichloromethane (25 mL) at ambient temperature. After stirred for 1 h, the reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated in vacuum. Purification by column chromatography (silica gel, hexane/EtOAc (2:1)) afforded the product as a white powder (0.572 g, 59%). 1H NMR (300 MHz, CDCl3) δ 8.25, 7.97, 7.65, 3.42, 2.36, 2.08, 1.91-1.59. The reaction mixture was evaporated in vacuo to dryness The solid residue was dissolved in dichloromethane (13 mL) After stirred for 1 h washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water The organic layer was dried over Na2SO4 evaporated in vacuum Purification by column chromatography (silica gel, hexane/EtOAc (2:1))

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100-mL round bottom flask, 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (0.64 g, 3.6 mmol), chloroform (14 mL), dimethylformamide (0.1 mL) and thionyl chloride (1.2 mL) were added. The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (13 mL) and added dropwise to the mixture of cyclobutylethylamine (0.47 g, 4.74 mmol) and triethylamine (0.8 mL) in dichloromethane (25 mL) at ambient temperature. After stirred for 1 h, the reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated in vacuum. Purification by column chromatography (silica gel, hexane/EtOAc (2:1)) afforded the product as a white powder (0.572 g, 59%). 1H NMR (300 MHz, CDCl3) δ 8.25, 7.97, 7.65, 3.42, 2.36, 2.08, 1.91-1.59. The reaction mixture was evaporated in vacuo to dryness The solid residue was dissolved in dichloromethane (13 mL) After stirred for 1 h washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water The organic layer was dried over Na2SO4 evaporated in vacuum Purification by column chromatography (silica gel, hexane/EtOAc (2:1))

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100-mL round bottom flask, 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (0.64 g, 3.6 mmol), chloroform (14 mL), dimethylformamide (0.1 mL) and thionyl chloride (1.2 mL) were added. The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (13 mL) and added dropwise to the mixture of cyclobutylethylamine (0.47 g, 4.74 mmol) and triethylamine (0.8 mL) in dichloromethane (25 mL) at ambient temperature. After stirred for 1 h, the reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated in vacuum. Purification by column chromatography (silica gel, hexane/EtOAc (2:1)) afforded the product as a white powder (0.572 g, 59%). 1H NMR (300 MHz, CDCl3) δ 8.25, 7.97, 7.65, 3.42, 2.36, 2.08, 1.91-1.59. The reaction mixture was evaporated in vacuo to dryness The solid residue was dissolved in dichloromethane (13 mL) After stirred for 1 h washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water The organic layer was dried over Na2SO4 evaporated in vacuum Purification by column chromatography (silica gel, hexane/EtOAc (2:1))

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100-mL round bottom flask, 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (0.64 g, 3.6 mmol), chloroform (14 mL), dimethylformamide (0.1 mL) and thionyl chloride (1.2 mL) were added. The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (13 mL) and added dropwise to the mixture of cyclobutylethylamine (0.47 g, 4.74 mmol) and triethylamine (0.8 mL) in dichloromethane (25 mL) at ambient temperature. After stirred for 1 h, the reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated in vacuum. Purification by column chromatography (silica gel, hexane/EtOAc (2:1)) afforded the product as a white powder (0.572 g, 59%). 1H NMR (300 MHz, CDCl3) δ 8.25, 7.97, 7.65, 3.42, 2.36, 2.08, 1.91-1.59. The reaction mixture was evaporated in vacuo to dryness The solid residue was dissolved in dichloromethane (13 mL) After stirred for 1 h washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water The organic layer was dried over Na2SO4 evaporated in vacuum Purification by column chromatography (silica gel, hexane/EtOAc (2:1))

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100-mL round bottom flask, 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (0.64 g, 3.6 mmol), chloroform (14 mL), dimethylformamide (0.1 mL) and thionyl chloride (1.2 mL) were added. The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (13 mL) and added dropwise to the mixture of cyclobutylethylamine (0.47 g, 4.74 mmol) and triethylamine (0.8 mL) in dichloromethane (25 mL) at ambient temperature. After stirred for 1 h, the reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated in vacuum. Purification by column chromatography (silica gel, hexane/EtOAc (2:1)) afforded the product as a white powder (0.572 g, 59%). The reaction mixture was evaporated in vacuo to dryness The solid residue was dissolved in dichloromethane (13 mL) After stirred for 1 h washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water The organic layer was dried over Na2SO4 evaporated in vacuum Purification by column chromatography (silica gel, hexane/EtOAc (2:1))

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100-mL round bottom flask, 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (0.64 g, 3.6 mmol), chloroform (14 mL), dimethylformamide (0.1 mL) and thionyl chloride (1.2 mL) were added. The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (13 mL) and added dropwise to the mixture of cyclobutylethylamine (0.47 g, 4.74 mmol) and triethylamine (0.8 mL) in dichloromethane (25 mL) at ambient temperature. After stirred for 1 h, the reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated in vacuum. Purification by column chromatography (silica gel, hexane/EtOAc (2:1)) afforded the product as a white powder (0.572 g, 59%). The reaction mixture was evaporated in vacuo to dryness The solid residue was dissolved in dichloromethane (13 mL) After stirred for 1 h washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water The organic layer was dried over Na2SO4 evaporated in vacuum Purification by column chromatography (silica gel, hexane/EtOAc (2:1))

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100-mL round bottom flask, 6-oxo-1,6-dihydropyridazine-3-carboxylic acid monohydrate (0.64 g, 3.6 mmol), chloroform (14 mL), dimethylformamide (0.1 mL) and thionyl chloride (1.2 mL) were added. The reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was evaporated in vacuo to dryness. The solid residue was dissolved in dichloromethane (13 mL) and added dropwise to the mixture of cyclobutylethylamine (0.47 g, 4.74 mmol) and triethylamine (0.8 mL) in dichloromethane (25 mL) at ambient temperature. After stirred for 1 h, the reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated in vacuum. Purification by column chromatography (silica gel, hexane/EtOAc (2:1)) afforded the product as a white powder (0.572 g, 59%). 1H NMR (300 MHz, CDCl3) δ 8.25, 7.97, 7.65, 3.42, 2.36, 2.08, 1.91-1.59. The reaction mixture was evaporated in vacuo to dryness The solid residue was dissolved in dichloromethane (13 mL) After stirred for 1 h washed sequentially with 10% aqueous HCl solution, saturated NaHCO3 and water The organic layer was dried over Na2SO4 evaporated in vacuum Purification by column chromatography (silica gel, hexane/EtOAc (2:1))