二乙基氨磺酰氯

反应条件: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine (145 mg, 0.38 mmol, cf. example 67) was dissolved in dry dichloromethane (8 mL). Triethylamine (60 μL, 0.45 mmol). The solution was cooled to 0-5° C. and diethylsulfamoyl chloride (71.5 mg, 0.42 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with dichloromethane (20 mL) and washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL). The organic layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:ethyl acetate=180:5). Yield: 96 mg (0.19 mmol, 48.9%). washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL) The organic layer was dried (MgSO4) the solvent was evaporated in vacuo The crude product was purified by flash chromatography (silica, dichloromethane

反应条件: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine (145 mg, 0.38 mmol, cf. example 67) was dissolved in dry dichloromethane (8 mL). Triethylamine (60 μL, 0.45 mmol). The solution was cooled to 0-5° C. and diethylsulfamoyl chloride (71.5 mg, 0.42 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with dichloromethane (20 mL) and washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL). The organic layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:ethyl acetate=180:5). Yield: 96 mg (0.19 mmol, 48.9%). washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL) The organic layer was dried (MgSO4) the solvent was evaporated in vacuo The crude product was purified by flash chromatography (silica, dichloromethane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of diethylamine hydrochloride (1 g) in sulfuryl chloride (10 ml) was heated at 50° C. for 4 hours. The solution was allowed to cool to ambient temperature and sulfuryl cloride was evaporated in vacuo. To the residue were added ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give diethylsulfamoyl chloride (720 mg) as a colorless oil. sulfuryl cloride was evaporated in vacuo To the residue were added ethyl acetate and water The organic layer was washed with brine dried over anhydrous magnesium sulfate concentrated in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: N,N-Disubstituted sulfamoyl chlorides were prepared as described by Binkley and Degering [J. Am. Chem. Soc., 61, 3250-3251 (1939)], herein incorporated by reference. For example, diethylamine (0.33 mole) was added very slowly to sulfuryl chloride (0.33 mole) with vigorous stirring and ice water chilling. The mixture was warmed and heated under reflux for 24 hours. The cooled mixture was extracted with anhydrous ethyl ether, and the extract was concentrated and the residue distilled under reduced pressure to afford N,N-diethyl sulfamoyl chloride, b.p. 69° (10 mmHg). N,N-Dimethyl-sulfamoyl chloride was purchased commercially. The mixture was warmed heated under reflux for 24 hours The cooled mixture was extracted with anhydrous ethyl ether the extract was concentrated the residue distilled under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: N,N-Disubstituted sulfamoyl chlorides were prepared as described by Binkley and Degering [J. Am. Chem. Soc., 61, 3250-3251 (1939)], herein incorporated by reference. For example, diethylamine (0.33 mole) was added very slowly to sulfuryl chloride (0.33 mole) with vigorous stirring and ice water chilling. The mixture was warmed and heated under reflux for 24 hours. The cooled mixture was extracted with anhydrous ethyl ether, and the extract was concentrated and the residue distilled under reduced pressure to afford N,N-diethyl sulfamoyl chloride, b.p. 69° (10 mmHg). N,N-Dimethyl-sulfamoyl chloride was purchased commercially. The mixture was warmed heated under reflux for 24 hours The cooled mixture was extracted with anhydrous ethyl ether the extract was concentrated the residue distilled under reduced pressure

反应条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 600 ml of a dichloroethane solution containing 150 g (0.87 mole) of 2-hydroxy-1-naphthaldehyde and 250 g (1.87 moles) of anhydrous aluminum chloride was stirred with heating at 50° C. To the solution was added dropwise 172.2 g (1 mole) of N,N-diethylsulfamoyl chloride. After the completion of the dropwise addition, the mixture was refluxed for 3 hours. After cooling to room temperature, the reaction mixture was poured into 1 liter of ice water. Methylene chloride was added to the mixture and it was extracted and separated. The organic layer was concentrated to about 500 ml. To the concentrate was added methanol to precipitate crystals. The precipitated crystals were collected by filtration, and washed with methanol to obtain 228 g (0.74 mole) of 2-hydroxy-6-(N,N-diethylsulfamoyl)-1-naphthaldehyde. After the completion of the dropwise addition the mixture was refluxed for 3 hours After cooling to room temperature was extracted separated The organic layer was concentrated to about 500 ml To the concentrate was added methanol to precipitate crystals The precipitated crystals were collected by filtration washed with methanol

反应条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 600 ml of a dichloroethane solution containing 150 g (0.87 mole) of 2-hydroxy-1-naphthaldehyde and 250 g (1.87 moles) of anhydrous aluminum chloride was stirred with heating at 50° C. To the solution was added dropwise 172.2 g (1 mole) of N,N-diethylsulfamoyl chloride. After the completion of the dropwise addition, the mixture was refluxed for 3 hours. After cooling to room temperature, the reaction mixture was poured into 1 liter of ice water. Methylene chloride was added to the mixture and it was extracted and separated. The organic layer was concentrated to about 500 ml. To the concentrate was added methanol to precipitate crystals. The precipitated crystals were collected by filtration, and washed with methanol to obtain 228 g (0.74 mole) of 2-hydroxy-6-(N,N-diethylsulfamoyl)-1-naphthaldehyde. After the completion of the dropwise addition the mixture was refluxed for 3 hours After cooling to room temperature was extracted separated The organic layer was concentrated to about 500 ml To the concentrate was added methanol to precipitate crystals The precipitated crystals were collected by filtration washed with methanol

反应条件: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine (145 mg, 0.38 mmol, cf. example 67) was dissolved in dry dichloromethane (8 mL). Triethylamine (60 μL, 0.45 mmol). The solution was cooled to 0-5° C. and diethylsulfamoyl chloride (71.5 mg, 0.42 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with dichloromethane (20 mL) and washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL). The organic layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:ethyl acetate=180:5). Yield: 96 mg (0.19 mmol, 48.9%). washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL) The organic layer was dried (MgSO4) the solvent was evaporated in vacuo The crude product was purified by flash chromatography (silica, dichloromethane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: N,N-Disubstituted sulfamoyl chlorides were prepared as described by Binkley and Degering [J. Am. Chem. Soc., 61, 3250-3251 (1939)], herein incorporated by reference. For example, diethylamine (0.33 mole) was added very slowly to sulfuryl chloride (0.33 mole) with vigorous stirring and ice water chilling. The mixture was warmed and heated under reflux for 24 hours. The cooled mixture was extracted with anhydrous ethyl ether, and the extract was concentrated and the residue distilled under reduced pressure to afford N,N-diethyl sulfamoyl chloride, b.p. 69° (10 mmHg). N,N-Dimethyl-sulfamoyl chloride was purchased commercially. The mixture was warmed heated under reflux for 24 hours The cooled mixture was extracted with anhydrous ethyl ether the extract was concentrated the residue distilled under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: N,N-Disubstituted sulfamoyl chlorides were prepared as described by Binkley and Degering [J. Am. Chem. Soc., 61, 3250-3251 (1939)], herein incorporated by reference. For example, diethylamine (0.33 mole) was added very slowly to sulfuryl chloride (0.33 mole) with vigorous stirring and ice water chilling. The mixture was warmed and heated under reflux for 24 hours. The cooled mixture was extracted with anhydrous ethyl ether, and the extract was concentrated and the residue distilled under reduced pressure to afford N,N-diethyl sulfamoyl chloride, b.p. 69° (10 mmHg). N,N-Dimethyl-sulfamoyl chloride was purchased commercially. The mixture was warmed heated under reflux for 24 hours The cooled mixture was extracted with anhydrous ethyl ether the extract was concentrated the residue distilled under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the manner given in Example 14, 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine is reacted with diethylsulfamoyl chloride, in the presence of triethylamine to give 1-[(diethylamino)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine.

反应条件: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine (145 mg, 0.38 mmol, cf. example 67) was dissolved in dry dichloromethane (8 mL). Triethylamine (60 μL, 0.45 mmol). The solution was cooled to 0-5° C. and diethylsulfamoyl chloride (71.5 mg, 0.42 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with dichloromethane (20 mL) and washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL). The organic layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:ethyl acetate=180:5). Yield: 96 mg (0.19 mmol, 48.9%). washed with a 1:1 mixture of water and saturated ammonium chloride solution (20 mL) The organic layer was dried (MgSO4) the solvent was evaporated in vacuo The crude product was purified by flash chromatography (silica, dichloromethane