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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
Structure of 42899-76-3 * Storage: {[proInfo.prStorage]}
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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 :

Calculated chemistry of [ 42899-76-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.29
TPSA : 55.41 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 0.24
Log Po/w (SILICOS-IT) : 0.91
Consensus Log Po/w : 1.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.62
Solubility : 0.514 mg/ml ; 0.0024 mol/l
Class : Soluble
Log S (Ali) : -2.55
Solubility : 0.601 mg/ml ; 0.00281 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.56
Solubility : 0.584 mg/ml ; 0.00273 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

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:
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.

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

[ 42899-76-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 42899-76-3 ]
  • [ 16133-25-8 ]
YieldReaction ConditionsOperation in experiment
92.9% at 85℃; 21.4 g (0.100 mol) of pyridine-3-sulfonyl chloride hydrochloride and 42.8 g of monochlorobenzene were placed in a 200 mL four-necked flask, and the slurry Liquid). The internal pressure was adjusted to 23 kPa using a vacuum pump and heated to 85 ± 5 ° C. for 5 hours (dehydrochlorination). After 5 hours, the contents of the flavor became almost transparent liquid. Thereafter, monochlorobenzene was distilled off under reduced pressure (100 ° C., 27 kPa). Subsequently, distillation under reduced pressure (110 ° C., 1 kPa) gave 16.5 g (0.0929 mol, yield 92.9percent) of pyridine-3-sulfonyl chloride.
Reference: [1] Patent: JP6165374, 2017, B1, . Location in patent: Paragraph 0019
[2] Patent: WO2008/54288, 2008, A1, . Location in patent: Page/Page column 90
  • 2
  • [ 42899-76-3 ]
  • [ 2922-45-4 ]
YieldReaction ConditionsOperation in experiment
91% With ammonia In methanol; dichloromethane at 20℃; for 0.833333 h; 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.
Reference: [1] Patent: WO2009/17822, 2009, A2, . Location in patent: Page/Page column 64
[2] Patent: WO2006/33446, 2006, A1, . Location in patent: Page/Page column 69
  • 3
  • [ 42899-76-3 ]
  • [ 65001-21-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1980, vol. 23, # 12, p. 1376 - 1380
[2] Patent: WO2011/88027, 2011, A1, . Location in patent: Page/Page column 69
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7431 - 7448
  • 4
  • [ 636-73-7 ]
  • [ 42899-76-3 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: at 120℃; for 15 h;
Stage #2: With hydrogenchloride In chloroform
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%
Stage #1: at 120℃; for 8 h;
Stage #2: With hydrogenchloride In chloroform at 20℃;
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) δ: 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 8 h; 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)δ: 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).
Reference: [1] Advanced Synthesis and Catalysis, 2004, vol. 346, # 8, p. 925 - 928
[2] Patent: WO2008/3703, 2008, A1, . Location in patent: Page/Page column 82
[3] Patent: US2007/60623, 2007, A1, . Location in patent: Page/Page column 24
[4] Patent: WO2006/36024, 2006, A1, . Location in patent: Page/Page column 160
[5] Patent: EP2336107, 2015, B1, . Location in patent: Paragraph 0306
[6] Phosphorus and Sulfur and the Related Elements, 1980, vol. 8, p. 189 - 196
[7] Journal of Medicinal Chemistry, 1989, vol. 32, # 11, p. 2436 - 2442
[8] Patent: US2003/69299, 2003, A1,
[9] Patent: US4315014, 1982, A,
[10] Patent: EP1803709, 2007, A1,
[11] Patent: WO2006/33446, 2006, A1, . Location in patent: Page/Page column 68-69
  • 5
  • [ 636-73-7 ]
  • [ 10026-13-8 ]
  • [ 42899-76-3 ]
Reference: [1] Patent: US6124314, 2000, A,
  • 6
  • [ 881674-56-2 ]
  • [ 42899-76-3 ]
  • [ 881677-11-8 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 10 - 35℃; for 0.5 h;
Stage #2: With 15-crown-5 In tetrahydrofuran; mineral oil for 0.5 h;
Stage #3: for 3 h;
Reference Example 245
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.
Saturated brine was added to the reaction mixture, 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)δ: 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).
78%
Stage #1: With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 45℃; for 5 h;
Stage #2: With hydrogenchloride In water; acetonitrile at 10 - 20℃; for 1.5 h;
A total of 0.5g, 4-dimethylaminopyridine 90mg, 5ml acetonitrile, take N, N-diisopropylethylamine1.5g with a small amount of acetonitrile dissolved in the above reaction bottle, take pyridine-3-sulfonyl chloride hydrochloride 1.1g, with 5mlAcetonitrile dissolved into the reaction flask, heated to 45 ° C stirring reaction 5h after cooling to room temperature, adding 5ml of water,The pH was adjusted to 5 with 0.5 N hydrochloric acid solution, and 20 ml of water was slowly added dropwise (at this time, a large amount of white solid precipitated)Stirring at room temperature for 0.5h, cooling to below 10 , stirring 1h, filtration, filter cake with a small amount of acetonitrile and water mixtureWashing, 50 ° C drying was V total of 0.69g, yield 78percent.
Reference: [1] Patent: WO2006/36024, 2006, A1, . Location in patent: Page/Page column 219-220; 295
[2] Patent: EP2336107, 2015, B1, . Location in patent: Paragraph 0419
[3] Patent: CN105440019, 2016, A, . Location in patent: Paragraph 0044; 0045
[4] Patent: EP1803709, 2007, A1,
  • 7
  • [ 42899-76-3 ]
  • [ 881677-11-8 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 0.5 h;
Stage #2: With 15-crown-5 In tetrahydrofuran at 20℃; for 0.5 h;
Stage #3: for 3 h;
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) δ: 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).
Reference: [1] Patent: US2007/60623, 2007, A1, . Location in patent: Page/Page column 29
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