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Chemical Structure| 42899-76-3 Chemical Structure| 42899-76-3
Chemical Structure| 42899-76-3

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CAS No.: 42899-76-3

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Product Details of [ 42899-76-3 ]

CAS No. :42899-76-3
Formula : C5H5Cl2NO2S
M.W : 214.07
SMILES Code : Cl.N1=CC(=CC=C1)[S](=O)(=O)Cl
MDL No. :MFCD04035552
InChI Key :VIVPWOMJFLICOZ-UHFFFAOYSA-N
Pubchem ID :12571517

Safety of [ 42899-76-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
Class:8
UN#:3261
Packing Group:Ⅲ

Application In Synthesis of [ 42899-76-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 42899-76-3 ]

[ 42899-76-3 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 636-73-7 ]
  • [ 42899-76-3 ]
YieldReaction ConditionsOperation in experiment
83% Intermediate 23; Pyridine-3-sulfonyl chloride hydrochloride; Pyridine-3 -sulfonic acid (3.00 g, 18.8 mmol) and PCl5 (4.79 g, 23.0 mmol) were mixed in POCI3 (6 mL). The reaction was stirred and refiuxed at 120 °C over night (15 h). Cooled to rt., diluted with CHCl3 (20 mL) and saturated with HCl (g). This gave a white precipitation, which was filtered off, washed with CHCl3 and dried under reduced pressure to give the title compound (3.36 g, 83percent) as a white powder.
81% Reference Example 29 pyridin-3-ylsulfonyl chloride hydrochloride; A mixture of 3-pyridinesulfonic acid (50.0 g), phosphorus pentachloride (80.0 g) and phosphorus oxychloride (100 mL) was stirred at 120° C. for 8 hr. Under a nitrogen atmosphere, the mixture was cooled to room temperature, and chloroform (dehydrated, 330 mL) was added. Hydrogen chloride was blown in, and the precipitated crystals were collected by filtration and washed with chloroform (dehydrated) to give the title compound as a white solid (yield 54.7 g, 81percent). 1H-NMR (DMSO-d6) delta: 8.03-8.07 (1H, m), 8.68 (1H, d, J=8.1 Hz), 8.87 (1H, d, J=5.7 Hz), 9.01 (1H, s).
81% With phosphorus pentachloride; trichlorophosphate; In chloroform; at 120℃; for 8h; Reference Example 132 Pyridin-3-ylsulfonyl chloride hydrochloride A mixture of 3-pyridinesulfonic acid (50.0 g), phosphorus pentachloride (80.0 g) and phosphorus oxychloride (100 mL) was stirred at 120°C for 8 hr. Under a nitrogen atmosphere, the mixture was cooled to room temperature, and chloroform (dehydrated, 330 mL) was added. Hydrogen chloride was blown in, and the precipitated crystals were collected by filtration and washed with chloroform (dehydrated) to give the title compound as a white solid (yield 54.7 g, 81percent). 1H-NMR (DMSO-d6)delta: 8.03-8.07 (1H, m), 8.68 (1H, d, J=8.1 Hz), 8.87 (1H, d, J=5.7 Hz), 9.01 (1H, s).
With phosphorus pentachloride; EXAMPLE XIII Pyridine-3-sulphonic Acid Chloride Hydrochloride 1 g (6.3 mmol) of pyridine-3-sulphonic acid and 1.4 g (6.7 mmol) of phosphorus pentachloride are stirred for 2 hours at 150° C. After cooling, excess phosphorus pentachloride is eliminated in vacuo. The crude product is further reacted immediately. Yield: 1.2 g (91percent of theory).
With phosphorus pentachloride; In chloroform; EXAMPLE 9 N-[6-[4-(3-pyridinylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinoyl]ampicillin A mixture of 34.0 g (0.21 mol) of 3-pyridinesulfonic acid and 47 g (0.24 mol) of phosphorus pentachloride is heated on the steam bath for 2 hrs and the phosphorus oxychloride is removed at reduced pressure to give an oil which crystallize upon addition of chloroform. The solid is filtered, washed with chloroform, and dried under high vacuum to give 38.2 g of 3-pyridinesulfonyl chloride hydrochloride.
With phosphorus pentachloride; trichlorophosphate; In chloroform; Reference Example 132 Pyridin-3-ylsulfonyl chloride hydrochloride A mixture of 3-pyridinesulfonic acid (50.0 g), phosphorus pentachloride (80.0 g) and phosphorus oxychloride (100 mL) was stirred at 120°C for 8 hr. Under a nitrogen atmosphere, the mixture was cooled to room temperature, and chloroform (dehydrated, 330 mL) was added. Hydrogen chloride was blown in, and the precipitated crystals were collected by filtration and washed with chloroform (dehydrated) to give the title compound as a white solid (yield 54.7 g, 81percent). 1H-NMR (DMSO-d6)delta: 8.03-8.07 (1H, m), 8.68 (1H, d, J=8.1 Hz), 8.87 (1H, d, J=5.7 Hz), 9.01 (1H, s).
With phosphorus pentachloride; trichlorophosphate; at 130℃; for 3.5h; Preparation 27; A mixture of 3-pyridinesulfonic acid (10.0 g), phosphorous pentachloride (13.1 g) and phosphoryl chloride (10.0 ml) was stirred at 1300C for 3.5 hours. The solution was evaporated and diluted with acetone. The solution was evaporated and poured into water (200 ml) and EPO <DP n="71"/>isopropyl ether (400 ml). The organic layer was separated, washed with brine twice, saturated sodium bicarbonate aqueous solution and brine and dried over magnesium sulfate. The solution was evaporated, covered with hexane (20 ml) and added hydrogen chloride in ethyl acetate (4N, 20 ml) dropwise with stirring. The resulting solid was collected by filtration and dried to give 3- pyridinesulfonyl chloride hydrochloride (9.49 g) .NMR (200 MHz, DMSO-d6, delta) : 8.12 (IH, dd, J=5, 8Hz), 8.72 (IH, dd, J=I.8, 3Hz), 8.95 (IH, d, J=5.5Hz),8.99 (IH, d, J=IHz), 14.25 (IH, br s)

  • 2
  • [ 88372-34-3 ]
  • [ 42899-76-3 ]
  • [ 143817-10-1 ]
  • 3
  • [ 42899-76-3 ]
  • [ 65001-21-0 ]
YieldReaction ConditionsOperation in experiment
With bromine; at 130℃; for 8h; PREPARATION 14 5-amino-A/-methyl-3-pyridinesulfonamideStep 1 . 5-bromo-3-pyridinesulfonyl chlorideA mixture of <strong>[42899-76-3]3-pyridinesulfonyl chloride hydrochloride</strong> (8.9 g, 44 mmol) and bromine (14 g, 88 mmol) was heated to 130 °C for 8 h. The mixture was cooled and used directly in the next step.
  • 5
  • [ 42899-76-3 ]
  • sodium 3-pyridinesulfinate [ No CAS ]
  • 6
  • 1-amino-3-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)-2-imidazolidinone toluenesulfonic acid salt [ No CAS ]
  • [ 42899-76-3 ]
  • 1-[(Pyridin-3-yl)sulfonylamino]-3-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)-2-imidazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With 4-methyl-morpholine; In dichloromethane; at 80℃; for 0.416667h;Microwaves; EXAMPLE 6 Compound 62: 1-[(Pyridin-3-yl)sulfonylamino]-3-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)-2-imidazolidinone 1-[(Pyridin-3-yl)sulfonylamino]-3-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)-2-imidazolidinone: 1-Amino-3-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)-2-imidazolidinone toluenesulfonic acid (0.3 g, 0.58 mmol) is stirred in dichloromethane (6 mL) and 3-pyridylsulfonylchloride HCl (135 mg, 0.63 mmol) is added followed by 4-methylmorpholine (0.2 mL). The mixture is heated in a microwave oven at 80° C. for 25 minutes. The mixture is evaporated and purified over silica (hexane/ethylacetate) to give the afford 0.12 g (41percent yield) of the desired product as a white solid. 1H NMR (DMSO-d6) delta 10.3 (s, 1H), 9.0 (s, 1H), 8.9 (d, J=6 Hz, 1H), 8.2 (d, J=7.8 Hz, 1H), 7.65 (m, 1H), 7.2 (d, J=7.8 Hz, 2H), 7.05, (d, J=7.8 Hz, 2H), 6.95 (d, J=7.8 Hz, 2H), 6.8 (d, J=7.8 Hz, 2H), 4.5 (t, J=7 Hz, 1H), 3.8 (s, 3H), 3.75 (s, 3H), 3.3 (m, 1H), 3.2 (m, 1H), 2.75 (m, 2H), 2.4 (m, 2H). Anal. calcd. for C24H26N4O5S: C, 59.74; H, 5.43; N, 11.61; found C, 59.60; H, 5.47; N, 11.37. FAB-HRMS calcd. 483.1702; found 483.1720 (MH+).
  • 7
  • [ 52488-36-5 ]
  • [ 42899-76-3 ]
  • [ 1001394-86-0 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In water; for 0.75h; Intermediate 24; 4-Bromo-l-(pyridine-3-ylsulfonyl)-lH-indole; Aq. 2M NaOH (1 mL) was added to a stirred mixture of <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong> (240 mg, 1.12 mmol; Intermediate 23), 4-bromoindole (200 mg, 1.02 mmol) <n="84"/>and tetrabutylammonium hydrogen sulfate (35 mg, 0.10 mmol). The reaction was stirred 45 min. and the layers were allowed to separate. The organic layer was washed twice with diluted aq. NaOH, dried and concentrated to get the title compound (325 mg, 95%) as an off white solid. MS (ESI+) for CnH9BrN2O2S m/z 337 (M+H)+.
  • 8
  • [ 1001395-43-2 ]
  • [ 42899-76-3 ]
  • 1-[5-methoxy-1-(pyridin-3-ylsulfonyl)-1H-indol-4-yl]-N,N-dimethylmethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% With sodium hydroxide; In dichloromethane; water; at 20℃; Example 178; l-[5-Methoxy-l-(pyridin-3-ylsulfonyl)-lH-indol-4-yl]-lambda/,lambda/-dimethylmethanamine; To a solution of l-(5-methoxy-lH-indol-4-yl)-lambda/,lambda/-dimethylmethanamine (30 mg, 0.15 mmol; Intermediate 97) and <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong> (43 mg, 0.20 mmol) in DCM (1 mL) 5 M NaOH (2 mL) was added. The reaction mixture was stirred at rt over night. The organic phase was collected and the solvent was removed under reduced pressure. Purification by preparative HPLC/UV (System B) afforded the title product (2 mg, 4percent) as a white solid. MS (ESI+) for Ci7Hi9N3O3S m/z 346 (M+H)+.
  • 9
  • [ 223490-70-8 ]
  • [ 42899-76-3 ]
  • 7-((4-butyl-benzyl)-(pyridine-3-sulfonyl)-amino)-heptanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; 7-((4-Butyl-benzyl)-(Pyridine-3-sulfonyl)-amino)-heptanoic acid methyl ester. A solution of 7-(4-butyl-benzylamino)-heptanoic acid methyl ester prepared of Example 1, Step A (0.10 g, 0.33 mmol), N,N-diisopropylethylamine (0.85 g 0.66 mmol) and <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong>, prepared of Preparation 2, (0.070 g, 0.33 mmol) in 3 mL CH2Cl2 was stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and the organic solution was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica gel (10percent EtOAc/hexanes to 30percent EtOAc/hexanes) to afford the title compound of Step B. 1H NMR (400 MHz, CDCl3) delta 9.01 (s, 1H), 8.75 (d, 1H), 8.04 (d, 1H), 7.41 (dd, 1H), 7.23 (m, 4H), 4.30 (s, 2H), 3.62 (s, 3H), 3.08 (t, 2H), 2.55 (t, 2H), 2.19 (t, 2H), 1.10-1.58 (m, 12H), 0.87 (t, 3H); MS 447 (M+1).
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; Step B: Amide Formation 7-((4-Butyl-benzyl)-(pyridine-3-sulfonyl)-amino)-heptanoic acid methyl ester. A solution of 7-(4-butyl-benzylamino)-heptanoic acid methyl ester prepared of Example 1, Step A (0.10 g, 0.33 mmol); N,N-diisopropylethylamine (0.85 g 0.66 mmol) and <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong>, prepared of Preparation 2, (0.070 g, 0.33 mmol) in 3 mL CH2Cl2 was stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and the organic solution was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica gel (10percent EtOAc/hexanes to 30percent EtOAc/hexanes) to afford the title compound of Step B. 1H NMR (400 MHz, CDCl3) delta 9.01 (s, 1H), 8.75 (d, 1H), 8.04 (d, 1H), 7.41 (dd, 1H), 7.23 (m, 4H), 4.30 (s, 2H), 3.62 (s, 3H), 3.08 (t, 2H), 2.55 (t, 2H), 2.19 (t, 2H), 1.10-1.58 (m, 12H), 0.87 (t, 3H); MS 447 (M+1).
  • 10
  • [ 223492-51-1 ]
  • [ 42899-76-3 ]
  • [ 223492-52-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0℃; for 2h; {3-[(4-Tert-Butyl-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy acetic acid tert-butyl ester. To a solution of {3-[(4-tert-butyl-benzylamino)-methyl]-phenoxy}acetic acid tert-butyl ester (10.0 g, 26.1 mmol), prepared in Step A, in CH2Cl2 (75 mL) at 0° C. was added triethylamine (8.0 mL, 57.4 mmol), and <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong> (6.10 g, 28.7 mmol), of Preparation 2. The mixture was stirred for 0.5 h, the ice bath was removed, and the mixture was stirred for an additional 1.5 h. A 1:1 solution of water:aqueous saturated sodium bicarbonate was added to the solution, and the product was extracted into CH2Cl2 (3.x.). The combined organic solutions were dried over MgSO4 and concentrated in vacuo and the product was purified via silica gel chromatography (2:1 Hex:EtOAc) to give the title compound of Step B (11.0 g) as a clear oil. 1H NMR (400 MHz, CDCl3) delta 9.01 (s, 1H), 8.75 (d, 1H), 7.97 (d, 1H), 7.38 (m, 1H), 7.11-7.23 (m, 3H), 6.97 (d, 2H), 6.71 (d, 1H), 6.65 (d, 1H), 6.60 (s, 1H), 4.40 (s, 2H), 4.32 (s, 4H), 1.48 (s, 9H), 1.26 (s, 9H); MS 525 (M+1).
  • 11
  • [ 210114-98-0 ]
  • [ 42899-76-3 ]
  • 5-(3-((3-(3-chloro-phenyl)-propyl)-(pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; Step A: Sulfonamide Formation 5-(3-((3-(3-Chloro-phenyl)-propyl)-(pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid methyl ester. A solution of 5-(3-(3-(3-chloro-phenyl)-propylamino)-propyl)-thiophene-2-carboxylic acid methyl ester (from Preparation 8, 0.0855 g, 0.243 mmol), triethylamine (0.0541 g 0.534 mmol), and <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong> (from Preparation 2, 0.0572 g, 0.267 mmol) in 10 mL CH2Cl2 combined at 0° C. was stirred at room temperature overnight. The organic solution was washed with water, saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound of Step A as an oil. MS 494 (M+1).
With triethylamine; In dichloromethane; 5-(3-((3-(3-Chloro-phenyl)-propyl)-(pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid methyl ester A solution of 5-(3-(3-(3-chloro-phenyl)-propylamino)-propyl)-thiophene-2-carboxylic acid methyl ester (from Preparation 8, 0.0855 g, 0.243 mmol), triethylamine (0.0541 g 0.534 mmol), and <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong> (from Preparation 2, 0.0572 g, 0.267 mmol) in 10 mL CH2Cl2 combined at 0° C. was stirred at room temperature overnight. The organic solution was washed with water, saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound of Step A as an oil. MS 494 (M+1).
  • 12
  • [ 210115-55-2 ]
  • [ 42899-76-3 ]
  • [ 144-55-8 ]
  • [ 574759-41-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; water; Step D {3-[(Pyridine-3-sulfonylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester. To a solution of (3-aminomethyl-phenoxy)-acetic acid tert-butyl ester (296 mg, 1.25 mmol) in CH2Cl2 at 0° C. was added <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong> (279 mg, 1.31 mmol) followed by Et3N (0.36 mL, 2.6 mmol). The reaction was stirred at room temperature for 24 h and was quenched with a 1:1 solution of water and saturated aqueous NaHCO3. The aqueous solution was washed with CH2Cl2 (3*). The combined organic solutions were dried (MgSO4), filtered, and concentrated. Medium pressure chromatography (1:1 hexanes:EtOAc) provided the title compound as a white solid (369.5 mg). 1H NMR (400 MHz, CDCl3) delta 9.04 (s, 1H), 8.75 (m, 1H), 8.09 (d, 1H), 7.44 (m, 1H), 7.15 (m, 1H), 6.76 (m, 3H), 5.23 (bs, 1H), 4.44 (s, 2H), 4.16 (d, 2H), 1.47 (s, 9H); MS 379 (M+1).
  • 13
  • [ 223491-30-3 ]
  • [ 42899-76-3 ]
  • (3-(((2-(3-chloro-phenoxy)-ethyl)-(pyridine-3-sulfonyl)-amino)-methyl)-phenyl)-acetic acid [ No CAS ]
  • [ 223491-31-4 ]
YieldReaction ConditionsOperation in experiment
7-[(4-Pyrazin-2-yl-benzyl)-(pyridine-3-sulfonyl)-amino]-heptanoic acid methyl ester The title compound of Step A was prepared from 7-(4-pyrazin-2-yl-benzylamino)-heptanoic acid methyl ester, of Step A, and <strong>[42899-76-3]pyridine-3-sulfonyl chloride hydrochloride</strong>, of Preparation 2, following the method of Exmaple 1, Step B. 1H NMR (400 MHz, CDCl3) delta 9.04 (d, 1H), 8.99 (d, 1H), 8.78 (m, 1H), 8.60 (dd, 1H), 8.49 (d, 1H), 8.08 (m, 1H), 7.95 (m, 2H), 7.46-7.39 (m, 3H), 4.40 (s, 2H), 3.60 (s, 3H), 3.14 (t, 2H), 2.18 (t, 2H), 1.45 (m, 2H), 1.36 (m, 2H), 1.12 (m, 4H).
  • 14
  • [ 42899-76-3 ]
  • [ 6153-39-5 ]
  • [ 197960-44-4 ]
YieldReaction ConditionsOperation in experiment
58% In dichloromethane; sodium hydrogencarbonate; a 5-Methyl-3-(3-pyridinylsulfonyloxy)phenol A mixture of orcinol monohydrate (1.42 g, 0.01 mol) and 3-pyridylsulfonyl chloride hydrochloride (2.13 g, 0.01 mol), as prepared in J. Am. Chem. Soc., 114:4889 (1992), in saturated aqueous sodium bicarbonate (17.5 mL) and dichloromethane (50 mL) was stirred rapidly at ambient temperature for 2 days. The dichloromethane was separated and the aqueous layer was extracted with ethyl acetate (3*25 mL). The ethyl acetate and dichloromethane extracts were combined and washed with brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was recrystallized from ether and hexane, collected by filtration, and dried under high vacuum to give 1.54 g of a white solid (58percent yield). 1 H-NMR (300 MHz, CDCl3) delta 9.03 (d, 1H), 8.88 (dd, 1H), 8.16 (dt, 1H), 7.5 (m, 1H), 6.57 (d, 1H), 6.42 (s, 1H), 6.32 (t, 1H), 2.24 (s, 3H).
  • 15
  • [ 636-73-7 ]
  • [ 10026-13-8 ]
  • [ 42899-76-3 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate; PREPARATION 1 Pyridine-3-sulfonyl chloride hydrochloride A mixture of pyridine-3-sulfonic acid (15.0 g), phosphorous pentachloride (24.0 g) and phosphorous oxychloride (30 mL) was heated to 120° C. for 16 h. The reaction was cooled to room temperature, and the resulting suspension was saturated with HCl (g). A white precipitate was collected, washed with CHCl3, and dried in vacuo to afford the title compound (15.6 g). 1 H NMR (400 MHz, DMSO) delta 8.98 (s, 1H), 8.85 (d, 1H), 8.66 (d, 1H), 8.02 (t, 1H).
  • 16
  • [ 42899-76-3 ]
  • [ 90-04-0 ]
  • N-(2-methoxyphenyl)-3-pyridinesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
662 mg (83.5%) With pyridine; In water; toluene; REFERENCE EXAMPLE 1 N-(2-Methoxyphenyl)-3-pyridinesulfonamide o-Anisidine (377 mg, 3.0 mmol) was dissolved in toluene (10 ml) to which were subsequently added pyridine (0.48 ml, 6.0 mmol) and <strong>[42899-76-3]3-pyridinesulfonylchloride hydrochloride</strong> (642 mg, 3.0 mmol) at room temperature. After 1.5 hours of stirring at 100° C., the resulting reaction solution was mixed with water (20 ml), adjusted to pH 7 to 8 with anhydrous sodium carbonate, extracted with ethyl acetate and then washed with water and saturated brine. After drying on anhydrous sodium carbonate and removing the solvent by evaporation, the resulting orange solid was purified by a silica gel column chromatography (ether:hexane=3:1) to obtain a light orange solid which was subsequently washed with an ether-hexane (1:3) mixture solution to obtain 662 mg (83.5percent) of the title compound in the form of colorless prism crystals. Melting point: 101.5°-103° C. IR (KBr): 3008, 2712, 1586, 1498, 1420, 1336, 1320, 1280, 1256, 1194, 1110, 1020, 762, 744, 600, 578, 544 cm-1 NMR (CDCl3) delta: 3.58 (3H, s), 6.71 (1H, dd, J=7.5 Hz, 2 Hz), 6.80-7.14 (3H, m) 7.31 (1H, dd, J=8 Hz, 5 Hz), 7.54 (1H, dd, J=7.5 Hz, 2 Hz), 7.96 (1H, dd, J=8 Hz, 2 Hz), 8.70 (1H, dd, J=5 Hz, 2 Hz), 8.93 (1H, d, J=2 Hz)
  • 17
  • [ 504-15-4 ]
  • [ 42899-76-3 ]
  • [ 197960-44-4 ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 48h; a) 5-Methyl-3-(3-pyridinylsulfoxy)phenol A mixture of orcinol monohydrate (1.42 g, 0.01 mol) and 3-pyridylsulfonyl chloride hydrochloride (2.13 g, 0.01 mol), as prepared in J. Am. Chem. Soc., 114:4889 (1992), in saturated aqueous sodium bicarbonate (17.5 mL) and dichloromethane (50 mL) was stirred rapidly at ambient temperature for 2 days. The dichloromethane was separated and the aqueous layer was extracted with ethyl acetate (3 x 25 mL). The ethyl acetate and dichloromethane extracts were combined and washed with brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was recrystallized from ether and hexane, collected by filtration, and dried under high vacuum to give 1.54 g of a white solid (58percent yield). 1H-NMR (300 MHz, CDCl3) delta 9.03 (d, 1 H), 8.88 (dd, 1 H), 8.16 (dt, 1 H), 7.5 (m, 1 H), 6.57 (d, 1 H), 6.42 (s, 1 H), 6.32 (t, 1 H), 2.24 (s, 3 H).
  • 18
  • [ 42899-76-3 ]
  • [ 881675-04-3 ]
YieldReaction ConditionsOperation in experiment
64% Reference Example 44 ethyl 5-bromo-2-methyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carboxylate; Ethyl 5-bromo-2-methyl-1H-pyrrole-3-carboxylate (2.26 g) was dissolved in tetrahydrofuran (100 mL), sodium hydride (60percent in oil, 1.16 g) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (5.90 mL) was added and the mixture was further stirred at the same temperature for 15 min. 3-Pyridinesulfonyl chloride hydrochloride (3.13 g) was added and the reaction mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1-->7:3) to give the title compound as a yellow oil (yield 2.31 g, 64percent). 1H-NMR (CDCl3) delta: 1.24-1.34 (3H, m), 2.94 (3H, s), 4.23-4.30 (2H, m), 6.69 (1H, s), 7.51-7.55 (1H, m), 8.17-8.21 (1H, m), 8.88-8.91 (1H, m), 9.14 (1H, m).
  • 19
  • [ 42899-76-3 ]
  • [ 881676-90-0 ]
YieldReaction ConditionsOperation in experiment
75% Reference Example 55 5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde; Under an argon atmosphere, 5-phenyl-1H-pyrrole-3-20 carbaldehyde (342 mg) was dissolved in absolute tetrahydrofuran (20 mL) and sodium hydride (60percent in oil, 240 mg) was added while stirring at room temperature. After stirring at the same temperature for 15 min, 15-crown-5 (1.21 mL) was added, and the mixture was further stirred at the same temperature for 15 min. Pyridin-3-ylsulfonyl chloride hydrochloride (642 mg) was added, and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1-->1:1) to give the title compound as a brown solid (yield 470 mg, 75percent). 1H-NMR (CDCl3) delta: 6.60 (1H, d, J=1.8 Hz), 7.15-7.19 (2H, m), 7.25-7.37 (3H, m), 7.42-7.48 (1H, m), 7.53-7.57 (1H, m), 8.13 (1H, d, J=1.8 Hz), 8.49-8.50 (1H, m), 8.74-8.76 (1H, m), 9.90 (1H, s).
  • 20
  • [ 42899-76-3 ]
  • [ 881677-11-8 ]
YieldReaction ConditionsOperation in experiment
82% Reference Example 63 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde; To a solution (96 mL) of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (475 mg) in tetrahydrofuran was added sodium hydride (60percent in oil, 503 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (2.77 g) was added dropwise and the mixture was stirred for 30 min. Pyridine-3-sulfonyl chloride hydrochloride (1.35 g) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with saturated brine, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3-->2:3) and crystallized from diisopropyl ether-ethyl acetate (4:1) to give the title compound as colorless crystals (yield 680 mg, 82percent). 1H-NMR (CDCl3) delta: 6.68 (1H, d, J=1.8 Hz), 6.99-7.05 (1H, m), 7.16-7.19 (2H, m), 7.35-7.39 (1H, m), 7.45-7.51 (1H, m), 7.69-7.73 (1H, m), 8.14 (1H, d, J=1.8 Hz), 8.58-8.59 (1H, m), 8.81-8.83 (1H, m), 9.91 (1H, s).
  • 21
  • [ 42899-76-3 ]
  • [ 881677-15-2 ]
YieldReaction ConditionsOperation in experiment
~ 100% Reference Example 64 1-(pyridin-3-ylsulfonyl)-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde; To a solution (36 mL) of 5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (240 mg) in tetrahydrofuran was added sodium hydride (60percent in oil, 201 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (1.11 g) was added dropwise and the mixture was stirred for 30 min. Pyridine-3-sulfonyl chloride hydrochloride (537 mg) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with saturated brine, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1-->2:3) and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 380 mg, about 100percent). 1H-NMR (CDCl3) delta: 6.69 (1H, d, J=11.8 Hz), 7.34-7.38 (1H, m), 7.44-7.48 (1H, m), 7.61-7.69 (4H, m), 8.16 (1H, d, J=1.8 Hz), 8.45 (1H, d, J=2.4 Hz), 8.81 (1H, m), 9.91 (1H, s).
  • 22
  • [ 42899-76-3 ]
  • [ 881677-34-5 ]
YieldReaction ConditionsOperation in experiment
53% Reference Example 65 4-methyl-5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde; 4-Methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg) was dissolved in tetrahydrofuran (10 mL), sodium hydride (60percent in oil, 60 mg) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (0.30 mL) was added and the mixture was further stirred at the same temperature for 15 min. 3-Pyridinesulfonyl chloride hydrochloride (231 mg) was added and the reaction mixture was stirred at room temperature for 1 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1-->1:1) to give the title compound as a colorless solid (yield 172 mg, 53percent). 1H-NMR (CDCl3) delta: 2.03 (3H, s), 7.01-7.04 (2H, m), 7.26-7.55 (5H, m), 8.07 (1H, s), 8.47 (1H, m), 8.75-8.78 (1H, m), 9.97 (1H, s).
  • 23
  • [ 42899-76-3 ]
  • [ 2922-45-4 ]
YieldReaction ConditionsOperation in experiment
91% With ammonia; In methanol; dichloromethane; at 20℃; for 0.833333h; Example 79; N-(6-(2-(pyridine-5-sulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide; Step 1. Pyridine-3 -sulfonamide; Pyridine-3-sulfonyl chloride HCl (647.2 mg, 3.023 mmol) was suspended in DCM (9.0 mL) and NH3 (5 mL, 7N in MeOH, 35 mmol) was added. The reaction was stirred at RT under nitrogen for 50 minutes and then filtered, and the solid was washed with DCM. The filtrate was concentrated and dried under high vacuum to provide pyridine-3 -sulfonamide (477 mg , 91percent yield). MS (ESI pos. ion) m/z: 159(MH+). Calculated exact mass for C5H6N2O2S: 158.
With ammonia; In acetone; at 0 - 20℃; for 3h; Preparation 28; To a suspension of <strong>[42899-76-3]3-pyridinesulfonyl chloride hydrochloride</strong> (5.00 g) in acetone (8.5 ml) was added ammonia aqueous solution (28percent, 8.5 ml) at 00C dropwise and stirred at room temperature for 3 hours. The solution was evaporated and poured into water (ca. 10 ml), ethyl acetate (100 ml) and tetrahydrofuran (100 ml). The organic layer was washed with brine twice and the aqueous layer was extracted with ethyl acetate (90 ml) and methanol (10 ml). The combined organic layer was dried over magnesium sulfate, evaporated and crystallized in hexane and ethyl acetate to give 3-pyridinesulfonamide (3.45 g) .(+)ESI-MS (m/z): 159 (M+H)+
  • 24
  • [ 76854-31-4 ]
  • [ 42899-76-3 ]
  • 6-[4-(3-pyridinylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chloro-trimethyl-silane; triethylamine; In methanol; dichloromethane; water; A suspension of 11.5 g (50 mmol) of 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 21 ml (150 mmol) of triethylamine, and 500 ml of dichloromethane is stirred at 0°-5° and 20.2 ml (158 mmol) of chlorotrimethylsilane is added. The ice bath is removed and the mixture is stirred at room temperature for 1 hr. The solution is cooled with an ice bath and 11.8 g (55 mmol) of <strong>[42899-76-3]3-pyridinesulfonyl chloride hydrochloride</strong> is added followed by 7 ml (50 mmol) of triethylamine 15 min later. The reaction is stirred at room temperature for 70 hrs, cooled with an ice bath and 3.5 ml (25 mmol) of triethylamine is added. The reaction is stirred at room temperature for 4.5 hrs, cooled with an ice bath, and 11.8 g (55 mmol) of <strong>[42899-76-3]3-pyridinesulfonyl chloride hydrochloride</strong> is added. The mixture is stirred at room temperature for 16 hrs and the dichloromethane is evaporated. Water is added to the residue and the precipitated solid is filtered, washed with water, ether, methanol, and ether, and dried to give 18.8 g of product. This material is combined with 3.2 g from another run and is heated with stirring at reflux for 1.5 hr with 450 ml of methanol. The solid is filtered, washed with methanol and ether and dried to give 19.8 g of 6-[4-(3-pyridinylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid; mp>260°.
  • 25
  • [ 76868-73-0 ]
  • [ 42899-76-3 ]
  • 6-[3-(3-pyridinylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; potassium carbonate; In water; EXAMPLE 10 N-[6-[3-(3-pyridinylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinoyl]ampicillin A suspension of 11.5 g (50 mmol) of 6-(3-aminophenyl)-1,2-dihydro-2-oxonicotinic acid and 300 ml of water is stirred at room temperature and 21 g (0.15 mol) of potassium carbonate is added. The solution is cooled to 25° and 13.0 g (61 mmol) of <strong>[42899-76-3]3-pyridinesulfonyl chloride hydrochloride</strong> is slowly added. The solution is clarified by filtration and the pH of the filtrate adjusted to 5.3 with hydrochloric acid. The precipitated solid is filtered, washed with water and dissolved in 300 ml of water containing 10 g (72 mmol) of potassium carbonate. The solution is stirred at room temperature and 10 g (47 mmol) of <strong>[42899-76-3]3-pyridinesulfonyl chloride hydrochloride</strong> is gradually added along with portions of potassium carbonate to maintain a pH of 8. Altogether 10 g (72 mmol) of potassium carbonate is added. The reaction is stirred for 30 min at room temperature and filtered. The pH of the filtrate is adjusted to 6 with hydrochloric acid and the solids filtered and washed with water. A second crop is obtained by lowering the pH of the filtrate to 4.0 and the solid is filtered. The two crops are combined with 200 ml of 1 N sodium hydroxide and heated on the steam bath for 1 hour and filtered. The filtrate is acidified to pH 5.7 with 1 N hydrochloric acid and the solid is filtered, washed with water, methanol, and ether and dried under high vacuum to give 15.2 g of 6-[3-(3-pyridinylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid; mp 305° dec.
YieldReaction ConditionsOperation in experiment
3.18g (0.02 mol) of pyridine-3-sulphonic acid (C5H5NSO3) was mixed with 8.34g (0.04 mol) of PCl5in a dry flask. The flask was protected from moisture and heated at 130-140°C under reflux with stirring for 2 hours. The reaction mixture was then cooled. The cold solidified reaction mixture was then triturated with CHCl3to remove PCl5and POCl3. The supernatant liquid was discarded. The triturating process was repeated using fresh CHCl3and the product was finally triturated with CHCl3saturated with hydrogen chloride. The hydrogen chloride was prepared by the slow addition of concentrated sulphuric acid (H2SO4) from a dropping funnel to sodium chloride in a round bottom flask. The round bottom flask was connected to the trituration reaction vessel by rubber tubing. A white powder formed, which was filtered, washed with CHCl3and finally dried in a vacuum. This process gave 3-pyridinesulphonylchloride-HCl (yield 3.05g, 85 percent) C5H4NSO2Cl, (Melting point: 141-143°C). This procedure is described by Reinhart F. E., J. Franklin. Ind. 236, 316-320 (1943).
  • 27
  • [ 42899-76-3 ]
  • [ 118-92-3 ]
  • 2-[2-(pyridin-3-ylsulphonylamino)phenyl]-4H-3,1-benzoxazin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.0% In pyridine; acetone; Example 10 (I13) A solution of <strong>[42899-76-3]pyridine-3-sulphonyl chloride hydrochloride</strong> (83.0 g; 0.31 mol) in pyridine (40 ml) was added dropwise to a solution of anthranilic acid (21.0 g; 0.153 mol) in pyridine (45 ml) at 45-55°C over a 1.5 hour period. The resulting reaction mixture was stirred at 50-60°C for a further 2 hours, and then for 18 hours at 15-20°C. Acetone (45 ml) was added and the precipitate was isolated by filtration. The solid was washed well with acetone (2 x 50 ml), 2M hydrochloric acid (50 ml), water (to pH 7) and finally acetone again (2 x 50 ml). Drying in vacuo gave the product as a pale-yellow solid (11.8 g). The material was crystallized from an ethyl acetate/dichloromethane mixture to give 2-[2-(3-pyridylsulphonylamino)phenyl]-4H-3,1-benzoxazin-4-one (10.8 g; 37.0percent yield; HPLC analysis 99.4percent w/w) as a pale-yellow powder. m.p. 221-222°C. I.R. (KBr disc): numax= 1760, 1600, 1245, 1155 and 760 cmmin1.
  • 28
  • [ 42899-76-3 ]
  • [ 928324-69-0 ]
YieldReaction ConditionsOperation in experiment
84% Reference Example 130 5-(2,6-difluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde; To a solution of 5-(2,6-difluorophenyl)-1H-pyrrole-3-carbaldehyde (420 mg) in tetrahydrofuran (42 mL) was added sodium hydride (60percent in oil, 244 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (1.34 g) was added dropwise and the mixture was stirred for 30 min. 3-Pyridylsulfonyl chloride hydrochloride (565 mg) was added, and the mixture was further stirred for 1 hr. The reaction mixture was diluted with saturated brine, and the mixture was extracted with ethyl acetate. The obtained extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3-->1:1), and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 590 mg, 84percent). 1H-NMR (CDCl3) delta: 6.76 (1H, d, J=1.9 Hz), 6.90-6.95 (2H, m), 7.40-7.52 (2H, m), 7.77-7.81 (1H, m), 8.18 (1H, d, J=1.9 Hz), 8.65-8.66 (1H, m), 8.85-8.87 (1H, m), 9.91 (1H, s).
  • 29
  • [ 42899-76-3 ]
  • [ 928324-70-3 ]
YieldReaction ConditionsOperation in experiment
97% Reference Example 131 5-(4-cyclohexylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde; Sodium hydride (60percent in oil, 68 mg) was added to a solution of 5-(4-cyclohexylphenyl)-1H-pyrrole-3-carbaldehyde (0.17 g) in tetrahydrofuran (12 mL) at room temperature. The mixture was stirred for 20 min, 3-pyridinesulfonyl chloride (0.19 g) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:2-->42:1) to give the title compound as crystals (yield 0.26 g, 97percent). 1H-NMR (CDCl3) delta: 1.21-1.53 (5H, m), 1.73-1.98 (5H, m), 2.50-2.60 (1H, m), 6.57 (1H, d, J=1.9 Hz), 7.03-7.09 (2H, m), 7.13-7.29 (3H, m), 7.48 (1H, ddd, J=8.3, 2.0, 1.9 Hz), 8.11 (1H, d, J=1.9 Hz), 8.49 (1H, d, J=2.3 Hz), 8.73 (1H, dd, J=4.8, 1.6 Hz), 9.89 (1H, s).
 

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