N-phenylsulfamoyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 66 g of the product obtained in Step 1 above are added to a suspension of 38.6 g of N,N-bis(2-chloroethyl)amine hydrochloride in 265 ml of xylene heated to 100° C. The reaction mixture is heated at 140° C. for 12 hours and, after cooling, filtered over a frit. The filtrate is concentrated and then purified by flash chromatography (eluant CH2Cl2/AcOEt: 95/5) to yield the expected product. The reaction mixture is heated at 140° C. for 12 hours after cooling filtered over a frit The filtrate is concentrated purified by flash chromatography (eluant CH2Cl2/AcOEt: 95/5)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 66 g of the product obtained in Step 1 above are added to a suspension of 38.6 g of N,N-bis(2-chloroethyl)amine hydrochloride in 265 ml of xylene heated to 100° C. The reaction mixture is heated at 140° C. for 12 hours and, after cooling, filtered over a frit. The filtrate is concentrated and then purified by flash chromatography (eluant CH2Cl2/AcOEt: 95/5) to yield the expected product. The reaction mixture is heated at 140° C. for 12 hours after cooling filtered over a frit The filtrate is concentrated purified by flash chromatography (eluant CH2Cl2/AcOEt: 95/5)

反応条件: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 25.2 g of chlorosulphonic acid are added slowly to a solution of 60.6 g of aniline in 316 ml of methylene chloride cooled to −5° C. When the addition is complete, the mixture is allowed to return to ambient temperature and the precipitate obtained is filtered off. After drying, the precipitate is taken up in 231 ml of toluene, and 45.1 g of phosphorus pentachloride are added gradually. The mixture is then refluxed for 3 hours 30 minutes and, after returning to ambient temperature, the precipitate formed is filtered off. The filtrate is concentrated to obtain the expected product. When the addition to return to ambient temperature the precipitate obtained is filtered off After drying 45.1 g of phosphorus pentachloride are added gradually The mixture is then refluxed for 3 hours 30 minutes after returning to ambient temperature the precipitate formed is filtered off The filtrate is concentrated

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

実験手順: A solution of 3 g (10 mmol) 4-(6-Bromo-hexyloxy)-piperidine hydrochloride and 3.44 g (18 mmol) of Phenylsulfamoyl chloride in 100 ml dry CH2Cl2 was treated with 6.95 ml (49.9 mmol) of triethylamine. The reaction was stirred for 4 h at RT, diluted with CH2Cl2 and washed with water. The organic phase was dried (MgSO4) and evaporated to yield 5.67 g (quantitative) of 4-(6-Bromo-hexyloxy)-piperidine-1-sulfonic acid phenylamide. washed with water The organic phase was dried (MgSO4) evaporated

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

実験手順: A suspension of sodium phenylsulfamate (200 mg, prepared according to the procedure of Audrieth and Sveda, J. Org. Chem., 1944, 9, 89) in dry toluene (5 mL), under a blanket of nitrogen, was treated with PCl5 (267 mg). After stirring at 80° C. for 20 hours the reaction mixture was allowed to cool to room temperature and then evaporated to give the title compound (100 mg) as a brown oil, which was used without further purification. prepared to cool to room temperature evaporated

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

実験手順: A suspension of sodium phenylsulfamate (200 mg, prepared according to the procedure of Audrieth and Sveda, J. Org. Chem., 1944, 9, 89) in dry toluene (5 mL), under a blanket of nitrogen, was treated with PCl5 (267 mg). After stirring at 80° C. for 20 hours the reaction mixture was allowed to cool to room temperature and then evaporated to give the title compound (100 mg) as a brown oil, which was used without further purification. prepared to cool to room temperature evaporated

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

実験手順: A suspension of 7-chloro-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt (100 mg, Reference Example 1) in dry acetonitrile (5 mL) was treated with dry triethylamine (0.20 mL), then with phenylsulfamoyl chloride (100 mg Reference Example 44). After stirring at room temperature for a further 1 hour the reaction mixture was evaporated and the residue then treated with water and dichloromethane. The organic phase was separated, then dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and dichloromethane (1:1 v/v) to give 7-chloro-6-phenyl-2-phenylsulfamoyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide (85 mg) as a white solid, m.p. 207–208° C. [Elemental analysis: C, 55.44; H, 4.34; N, 12.78%; Calculated for C20H19ClN4O3S: C, 55.75; H, 4.44; N, 13.00%]. was evaporated the residue then treated with water and dichloromethane The organic phase was separated dried over magnesium sulfate evaporated The residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and dichloromethane (1:1 v/v)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir: