hexane-1-sulfonyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.10 mmol) in pyridine (3 mL) was added hexanesulfonyl chloride (0.022 mL, 0.12 mmol). After heating at 60° C. for 20 h, the mixture was diluted with ethyl acetate (100 mL), washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a white solid (3.8 mg, 8% yield). 1H NMR (300 MHz, CDCl3) δ 7.66, 7.29, 4.08, 3.91, 3.38, 3.27, 3.08, 1.84, 1.35, 1.27, 0.87. MS (ES+) m/z 499.4 (M+1). washed with brine dried over anhydrous MgSO4 concentrated in vacuo Purification by preparative thin layer chromatography

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

実験手順: To a solution of 2-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride (212 mg) in pyridine-DMF (8:1, 9 mL) was added hexanesulfonyl chloride (180 mg) under ice-cooling, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the residue, followed by extraction with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]hexane-1-sulfonamide (56 mg). cooling The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the residue followed by extraction with ethyl acetate (100 mL) The organic layer was washed sequentially with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

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

実験手順: A solution of 3.7 grams (0.02 Mol) hexane sulfonyl chloride, 3.2 grams (0.02 Mol) 4-aminobenzoylacetonitrile and 5 mL of pyridine was stirred at 0° C. for 1.5 hours. The resulting very thick brown solution was dissolved in 15 mL of methanol and dropwise added to 100 mL of 2N hydrochloric acid at 0° C. A tan precipitate formed which was stirred for 30 minutes, then filtered and washed with water and dried for 2 hours at 50° C./10 mm Hg to give 6.9 grams of crude product. This was recrystallized from aqueous ethanol to give 4.2 grams (13.6 mMol, 68% yield) of pure product, m.p.=125°-127° C. A tan precipitate formed which filtered washed with water dried for 2 hours at 50° C./10 mm Hg to give 6.9 grams of crude product This was recrystallized from aqueous ethanol

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

実験手順: In dry tetrahydrofuran (250 ml) 3 g (5.9 mmol) of [6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone hydrochloride was suspended and 10 mg of DMAP was added. Triethylamine (4 g, 40 mmol) was then added and the reaction mixture was stirred for 20 minutes at room temperature under a nitrogen blanket. n-Hexylsulfonyl chloride (3.6 g, 19.6 mmol) in 25 ml of tetrahydrofuran was slowly added to the reaction mixture. The reaction was allowed to proceed at room temperature and under nitrogen for 3 days. The reaction mixture was evaporated down in vacuo and resuspended in ethyl acetate and washed with water. The organic layer was dried by filtering it through anhydrous sodium sulfate and evaporated to a yellow oil. The oil was dissolved in chloroform and chromatographed (HPLC) on a silica gel column and eluted with a linear gradient starting with chloroform and ending with chloroform-methanol (19:1 v/v). The desired fractions were determined by thin layer chromatography, combined and evaporated down to afford 3.14 g of the title compound as a thick oil. to proceed at room temperature and under nitrogen for 3 days The reaction mixture was evaporated down in vacuo washed with water The organic layer was dried by filtering it through anhydrous sodium sulfate evaporated to a yellow oil The oil was dissolved in chloroform chromatographed (HPLC) on a silica gel column eluted with a linear gradient evaporated down

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

実験手順: Sulfonation of aniline 17 by hexane-1-sulfonyl chloride following the method used in Example 6 gives tert-butyl 3-(3-(hexylsulfonamido)phenyl)propylcarbamate.

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.10 mmol) in pyridine (3 mL) was added hexanesulfonyl chloride (0.022 mL, 0.12 mmol). After heating at 60° C. for 20 h, the mixture was diluted with ethyl acetate (100 mL), washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a white solid (3.8 mg, 8% yield). 1H NMR (300 MHz, CDCl3) δ 7.66, 7.29, 4.08, 3.91, 3.38, 3.27, 3.08, 1.84, 1.35, 1.27, 0.87. MS (ES+) m/z 499.4 (M+1). washed with brine dried over anhydrous MgSO4 concentrated in vacuo Purification by preparative thin layer chromatography

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

実験手順: To a solution of 2-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride (212 mg) in pyridine-DMF (8:1, 9 mL) was added hexanesulfonyl chloride (180 mg) under ice-cooling, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the residue, followed by extraction with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]hexane-1-sulfonamide (56 mg). cooling The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the residue followed by extraction with ethyl acetate (100 mL) The organic layer was washed sequentially with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

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

実験手順: To a solution of 2-(aminomethyl)-3-methylquinolin-4(1H)-one dihydrochloride (212 mg) in pyridine-DMF (8:1, 9 mL) was added hexanesulfonyl chloride (180 mg) under ice-cooling, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the residue, followed by extraction with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl)methyl]hexane-1-sulfonamide (56 mg). cooling The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the residue followed by extraction with ethyl acetate (100 mL) The organic layer was washed sequentially with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

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

実験手順: A solution of 3.7 grams (0.02 Mol) hexane sulfonyl chloride, 3.2 grams (0.02 Mol) 4-aminobenzoylacetonitrile and 5 mL of pyridine was stirred at 0° C. for 1.5 hours. The resulting very thick brown solution was dissolved in 15 mL of methanol and dropwise added to 100 mL of 2N hydrochloric acid at 0° C. A tan precipitate formed which was stirred for 30 minutes, then filtered and washed with water and dried for 2 hours at 50° C./10 mm Hg to give 6.9 grams of crude product. This was recrystallized from aqueous ethanol to give 4.2 grams (13.6 mMol, 68% yield) of pure product, m.p.=125°-127° C. A tan precipitate formed which filtered washed with water dried for 2 hours at 50° C./10 mm Hg to give 6.9 grams of crude product This was recrystallized from aqueous ethanol

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

実験手順: A solution of 3.7 grams (0.02 Mol) hexane sulfonyl chloride, 3.2 grams (0.02 Mol) 4-aminobenzoylacetonitrile and 5 mL of pyridine was stirred at 0° C. for 1.5 hours. The resulting very thick brown solution was dissolved in 15 mL of methanol and dropwise added to 100 mL of 2N hydrochloric acid at 0° C. A tan precipitate formed which was stirred for 30 minutes, then filtered and washed with water and dried for 2 hours at 50° C./10 mm Hg to give 6.9 grams of crude product. This was recrystallized from aqueous ethanol to give 4.2 grams (13.6 mMol, 68% yield) of pure product, m.p.=125°-127° C. A tan precipitate formed which filtered washed with water dried for 2 hours at 50° C./10 mm Hg to give 6.9 grams of crude product This was recrystallized from aqueous ethanol

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.10 mmol) in pyridine (3 mL) was added hexanesulfonyl chloride (0.022 mL, 0.12 mmol). After heating at 60° C. for 20 h, the mixture was diluted with ethyl acetate (100 mL), washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a white solid (3.8 mg, 8% yield). 1H NMR (300 MHz, CDCl3) δ 7.66, 7.29, 4.08, 3.91, 3.38, 3.27, 3.08, 1.84, 1.35, 1.27, 0.87. MS (ES+) m/z 499.4 (M+1). washed with brine dried over anhydrous MgSO4 concentrated in vacuo Purification by preparative thin layer chromatography