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[ CAS No. 42899-76-3 ] {[proInfo.proName]}

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Chemical Structure| 42899-76-3
Chemical Structure| 42899-76-3
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Product Details of [ 42899-76-3 ]

CAS No. :42899-76-3 MDL No. :MFCD04035552
Formula : C5H5Cl2NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :VIVPWOMJFLICOZ-UHFFFAOYSA-N
M.W : 214.07 Pubchem ID :12571517
Synonyms :

Safety of [ 42899-76-3 ]

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

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   1~12

  • 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).
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