1-isocyanato-1,2,3,4-tetrahydronaphthalene

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: To a stirred solution of 2.42 grams (0.04 mole) of ethanolamine in 200 ml. of ether is added a solution of 6.95 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 150 ml. of ether over a period of 30 minutes. Additional ether is added to facilitate stirring as the product precipitates. One hour after the isocyanate addition is complete, the mixture is filtered. The filter cake is washed with ether and dried to give 8.61 grams white solid, melting point 146° to 149° C. Recrystallization from nitromethane gives the analytical sample, melting point 147° C. to 149° C. Analysis calculated for C13H18N2O2 : C, 66.64; H, 7.74; N, 11.96. Found: C, 66.35; H, 7.78; N, 11.90. precipitates One hour after the isocyanate addition the mixture is filtered The filter cake is washed with ether dried

反応条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an ice cold, stirred mixture of 6.7 grams (0.080 mole) of methoxyamine hydrochloride in 80 ml. of methylene chloride is added a solution of 8.1 grams (0.080 mole) of triethylamine in 20 ml. of methylene chloride. The mixture is stirred at 15° C. for 15 minutes, and is then allowed to warm to 15° to 25° C. while a solution of 6.94 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 25 ml. of methylene chloride is added dropwise. The mixture is stirred for 30 minutes at room temperature and then filtered. The filtrate is washed with water, dried sodium sulfate, and the solvent evaporated at reduced pressure to give a solid. Recrystallization of the solid from acetone/hexane gives 6.75 grams of the product, melting point 122° to 125° C. Recrystallization of the product from acetone/hexane gives the analytical sample, melting point 123.5° to 125° C. Analysis Calculated for C12H16N2O2 : C, 65.43; H, 7.32; N, 12.72. Found: C, 65.32; H, 7.33; N, 12.64. The mixture is stirred for 30 minutes at room temperature filtered The filtrate is washed with water, dried sodium sulfate the solvent evaporated at reduced pressure to give a solid Recrystallization of the solid from acetone/hexane

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: In analogy to example 1c, 200 mg (1.089 mmol) of 6-chloro-4-methyl-1H-pyrazolo-[3,4-b]pyridin-3-ol were reacted with 226.4 mg (1.2 mmol) of 1-isocyanato-1,2,3,4-tetrahydronaphthalene in THF/DMF at RT. Yield: 142 mg (37%), M+H+: 357.35.

反応条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an ice-cold, stirred mixture of 6.7 grams (0.080 mole) of methoxyamine hydrochloride in 80 ml of methylene chloride is added a solution of 8.1 grams (0.080 mole) of triethylamine in 20 ml of methylene chloride. The mixture is stirred at 15°C. for 15 minutes, and is then allowed to warm to 15°C. to 25°C. while a solution of 6.94 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 25 ml of methylene chloride is added dropwise. The mixture is stirred for 30 minutes at room temperature and then filtered. The filtrate is washed with water, dried (sodium sulfate), and the solvent evaporated at reduced pressure to give a solid. Recrystallization of the solid from acetone/hexane gives 6.75 grams of the product, melting point 122°C. to 125°C. Recrystallization of the product from acetone/hexane gives the analytical sample, melting point 123.5°C. to 125°C. is added dropwise The mixture is stirred for 30 minutes at room temperature filtered The filtrate is washed with water dried (sodium sulfate) the solvent evaporated at reduced pressure to give a solid Recrystallization of the solid from acetone/hexane

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

実験手順: To a stirred solution of 242.4 grams (2.46 moles) of phosgene in 200 ml of toluene and 600 ml of benzene is slowly added a solution of 119.9 grams (0.814 mole) of 1,2,3,4-tetrahydro-1-naphthylamine, while maintaining the reaction temperature at 10°C. to 15°C. The mixture is stirred overnight at room temperature and then heated to reflux under a nitrogen atmosphere. After 4 hours reflux, most of the solvent is distilled from the reaction at atmospheric pressure. The residual solvent is evaporated at reduced pressure. The crude product is distilled to give 121.4 grams of product with boiling point 90°C. to 96°C. (0.3 mm). while maintaining the reaction temperature at 10°C. to 15°C heated to reflux under a nitrogen atmosphere After 4 hours reflux, most of the solvent is distilled from the reaction at atmospheric pressure The residual solvent is evaporated at reduced pressure The crude product is distilled

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

実験手順: To a stirred solution of 2.42 grams (0.04 mole) of ethanolamine in 200 ml. of ether is added a solution of 6.95 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 150 ml. of ether over a period of 30 minutes. Additional ether is added to facilitate stirring as the product precipitates. One hour after the isocyanate addition is complete, the mixture is filtered. The filter cake is washed with ether and dried to give 8.61 grams white solid, melting point 146°C. to 149°C. Recrystallization from nitromethane gives the analytical sample, melting point 147°C. to 149°C. Analysis calculated for C13H18N2O2 : C, 66.64; H, 7.74; N, 11.96. Found: C, 66.35; H, 7.78; N, 11.90. precipitates One hour after the isocyanate addition the mixture is filtered The filter cake is washed with ether dried

反応条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an ice cold, stirred mixture of 6.7 grams (0.080 mole) of methoxyamine hydrochloride in 80 ml. of methylene chloride is added a solution of 8.1 grams (0.080 mole) of triethylamine in 20 ml. of methylene chloride. The mixture is stirred at 15°C. for 15 minutes, and is then allowed to warm to 15°C. to 25°C. while a solution of 6.94 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 25 ml. of methylene chloride is added dropwise. The mixture is stirred for 30 minutes at room temperature and then filtered. The filtrate is washed with water, dried sodium sulfate, and the solvent evaporated at reduced pressure to give a solid. Recrystallization of the solid from acetone/hexane gives 6.75 grams of the product, melting point 122°C. to 125°C. Recrystallization of the product from acetone/hexane gives the analytical sample, melting point 123.5°C. to 125°C. Analysis Calculated for C12H16N2O2 : C, 65.43; H, 7.32; N, 12.72. Found: C, 65.32; H, 7.33; N, 12.64. The mixture is stirred for 30 minutes at room temperature filtered The filtrate is washed with water, dried sodium sulfate the solvent evaporated at reduced pressure to give a solid Recrystallization of the solid from acetone/hexane

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

実験手順: To a stirred solution of 2.42 grams (0.04 mole) or ethanolamine in 200 ml. of ether is added a solution of 6.95 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 150 ml. of ether over a period of 30 minutes. Additional ether is added to facilitate stirring as the product precipitates. One hour after the isocyanate addition is complete, the mixture is filtered. The filter cake is washed with ether and dried to give 8.61 grams white solid, melting point 146° C. to 149° C. Recrystallization from nitromethane gives the analytical sample, melting point 147° to 149° C. Analysis calculated for C13H18N2O2 : C, 66.64; H, 7.74; N, 11.96. Found: C, 66.35; H, 7.78, N, 11.90. precipitates One hour after the isocyanate addition the mixture is filtered The filter cake is washed with ether dried

反応条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an ice cold, stirred mixture of 6.7 grams (0.080 mole) of methoxyamine hydrochloride in 80 ml. of methylene chloride is added a solution of 8.1 grams (0.080 mole) of triethylamine in 20 ml. of methylene chloride. The mixture is stirred at 15° C. for 15 minutes, and is then allowed to warm to 15° to 25° C. while a solution of 6.94 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 25 ml. of methylene chloride is added dropwise. The mixture is stirred for 30 minutes at room temperature and then filtered. The filtrate is washed with water, dried sodium sulfate, and the solvent evaporated at reduced pressure to give a solid. Recrystallization of the solid from acetone/hexane gives 6.75 grams of the product, melting point 122° to 125° C. Recrystallization of the product from acetone/hexane gives the analytical sample, melting point 123.5° to 125° C. Analysis Calculated for C12H16N2O2 : C, 65.43; H, 7.32; N, 12.72. C, Found: C, 65.32; H, 7.33; N, 12.64. The mixture is stirred for 30 minutes at room temperature filtered The filtrate is washed with water, dried sodium sulfate the solvent evaporated at reduced pressure to give a solid Recrystallization of the solid from acetone/hexane

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

実験手順: To a stirred solution of 2.42 grams (0.04 mole) of ethanolamine in 200 ml. of ether is added a solution of 6.95 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 150 ml. of ether over a period of 30 minutes. Additional ether is added to facilitate stirring as the product precipitates. One hour after the isocyanate addition is complete, the mixture is filtered. The filter cake is washed with ether and dried to give 8.61 grams white solid, melting point 146° to 149° C. Recrystallization from nitromethane gives the analytical sample, melting point 147° C. to 149° C. Analysis calculated for C13H18N2O2 : C, 66.64; H, 7.74; N, 11.96. Found: C, 66.35; H, 7.78; N, 11.90. precipitates One hour after the isocyanate addition the mixture is filtered The filter cake is washed with ether dried