[ CAS No. 1083326-55-9 ] {[proInfo.proName]}

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Quality Control of [ 1083326-55-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1083326-55-9 ]

Product Details of [ 1083326-55-9 ]

CAS No. :	1083326-55-9	MDL No. :	MFCD12923396
Formula :	C₁₇H₂₀BClN₂O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	394.68	Pubchem ID :	-
Synonyms :

Safety of [ 1083326-55-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1083326-55-9 ]

* 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 [ 1083326-55-9 ]

[ 1083326-55-9 ] Synthesis Path-Downstream 1~10

1
[ 7752-82-1 ]
[ 1083326-55-9 ]
[ 1148008-29-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 105℃; for 18h;	b) lambda/-[5-(2-amino-5-pyrimidinyl)-2-chloro-3-pyridinyl]benzenesulfonamide; To a 25 mL seal tube (t=g) was added N-[2-chloro-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (131 mg, 0.33 mmol), 2- amino-5-bromopyrimidine (57 mg, 0.33 mmol), and potassium carbonate (138 mg, 1 <n="62"/>mmol) in 1,4-dioxane (8 ml) and water (4 ml). The reaction mixture was degassed by nitrogen, and tetrakis(triphenylphosphine)palladium(0) (14.64 mg, 0.013 mmol) was added. The tube was sealed and the reaction mixture was heated to 105 0C for 18 hr . Water (1 mL) followed by ethyl acetate (15 mL) and acetic acid (0.5 mL) were added. Organic layer was separated, washed with sat NaCl, dried over MgSO4, filtered and evaporated. Product purified by prep. HPLC (0.1% formic acid, 5 to 95% water :acetonitrile). Fractions were combined and evaporated. N-[5-(2-amino-5- pyrimidinyl)-2-chloro-3-pyridinyl]benzenesulfonamide (48 mg, 40 % yield) was isolated as a white solid. IH NMR (400 MHz, DMSO-J6) delta ppm 7.01 (s, 2 H) 7.58 (t, J=7.58 Hz, 2 H) 7.62 - 7.72 (m, 1 H) 7.72 - 7.80 (m, 2 H) 7.85 (d, J=2.27 Hz, 1 H) 8.49 (d, J=2.27 Hz, 1 H) 8.53 (s, 2 H) 10.38 (br. s., 1 H) LC-MS (m/e) = 362.0 (MH+). Rt = 1.19 min

Reference： [1]Patent: WO2009/55418,2009,A1 .Location in patent: Page/Page column 60-61

2
[ 1083326-55-9 ]
[ 89892-21-7 ]
[ 1093818-79-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;dichloro-1,1'-bis(diphosphino)ferrocene-palladium(II); In 1,4-dioxane; water; at 100℃; for 20h;	Example 67; JV-[2-Chloro-5-(4-oxo- 1 ,4-dihydro-6-quinazolinyl)-3-pyridinyl]benzenesulfonamidea) lambda/-[2-chloro-5-(6-quinazolinyl)-3-pyridinyl]benzenesulfonamide; A slurry of N-(5-bromo-2-chloro-3-pyridinyl)benzenesulfonamide (493 mg, 1.418 mmol), bis(pinacolato)diboron (375 mg, 1.477 mmol), potassium acetate (232 mg, 2.363 mmol) and PdCl2(dppf)-CH2Cl2 (48.2 mg, 0.059 mmol) in anhydrous 1,4- dioxane (9.60 mL) was heated at 100 0C for 6 h. The reaction was cooled slightly then treated with <strong>[89892-21-7]6-bromoquinazoline</strong> (247 mg, 1.182 mmol), 2 M aqueous sodium carbonate (2.363 mL, 4.73 mmol) and another portion of PdCl2(dppf)-CH2Cl2 (48.2 mg, 0.059 mmol) then heated at 100 0C for a further 20 h. The reaction was cooled to room temperature then concentrated under reduced pressure. The resulting crude residue was slurried in ethyl acetate then treated with decolorizing charcoal and <n="81"/>anhydrous sodium sulfate. Filtered through a short pad of silica then the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography with 40% hexanes in ethyl acetate. The combined, desired fractions were evaporated to give the product (236 mg, 49.8%) as a white solid. MS(ES)+ m/e 396.7 [M+H]+. IH NMR (400 MHz, DMSO-J6) delta ppm 7.60 (t, J=7.58 Hz, 3 H) 7.66 - 7.74 (m, 1 H) 7.78 (d, J=7.07 Hz, 2 H) 7.77 (s, 1 H) 8.12 - 8.21 (m, 3 H) 8.34 (dd, J=8.84, 2.27 Hz, 1 H) 8.51 (d, J=2.02 Hz, 1 H) 8.76 (d, J=2.27 Hz, 1 H) 9.36 (s, 1 H) 9.70 (s, 1 H) 10.54 (s, 1 H).

Reference： [1]Patent: WO2009/55418,2009,A1 .Location in patent: Page/Page column 79-80

3
[ 1083326-55-9 ]
[ 89466-22-8 ]
N-(6-chloro-6’-(methylsulfonamido)-[3,3’-bipyridin]-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Microwave irradiation;

Reference： [1]Yang, Chengbin; Zhang, Xi; Wang, Yi; Yang, Yongtai; Liu, Xiaofeng; Deng, Mingli; Jia, Yu; Ling, Yun; Meng, Ling-Hua; Zhou, Yaming [ACS Medicinal Chemistry Letters, 2017, vol. 8, # 8, p. 875 - 880]

4
[ 1083326-55-9 ]
[ 1111638-02-8 ]
N-(2-chloro-5-(2-methyl-1H-pyrrolo[2,3-b]pyridine-5-yl)pyridine-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 25 - 60℃; for 0.05h;	(3) <strong>[1111638-02-8]2-methyl-5-bromo-7-azaindole</strong> (0.15 g, 0.72 mmol) and tetrakis(triphenylphosphine)palladium (0.017 g, 0.014 mmol), potassium carbonate (0.20 g, 1.44 mmol) Dissolved in 1,4-dioxane (1.2mL) to prepare reaction solution 4. The flow rate (0.1mL / min) set by the intelligent numerical control sampler was passed through a polytetrafluoroethylene tube with an inner diameter of 1000 mum and the aforementioned The second effluent was simultaneously mixed into a third three-way mixer (ambient temperature: 25 C), and then entered into a polytetrafluoroethylene tube with an inner diameter of 1000 mum at a set temperature control (60 C) under its own pressure. The Suzuki coupling reaction between the second effluent product and 5-bromo-7-azaindole was completed within the set residence time t3 (3min), Obtaining the final effluent containing the target product N-{2-chloro-5-[2-methyl-1H-pyrrolo(2,3-b)pyridin-5-yl]pyridin-3-yl}benzenesulfonamide. (4) The above effluent, the solvent was distilled off under reduced pressure, and then separated through a silica gel column by column chromatography (DCM / MeOH, 3: 1), and then the solvent was distilled off under reduced pressure to obtain the target product N-{2-chloro-5-[2-methyl-1H-pyrrolo(2,3-b)pyridin-5-yl]pyridin-3-yl}benzenesulfonamide, yield 81%, purity 99%

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 875 - 880
[2]Patent: CN110498798,2019,A .Location in patent: Paragraph 0068-0069; 0072-0073

5
[ 875781-17-2 ]
[ 1083326-55-9 ]
N-{2-chloro-5-[1H-pyrazolo(3,4-b)pyridin-5-yl]pyridin-3-yl}benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 25 - 80℃; for 0.0166667h;	(3) 5-bromopyridopyrazole (0.14 g, 0.72 mmol) and tetrakis(triphenylphosphine)palladium (0.017 g, 0.014 mmol), potassium carbonate (0.20 g, 1.44 mmol) Dissolved in 1,4-dioxane (1.2mL) to prepare reaction solution 4. The flow rate (0.1mL / min) set by the intelligent numerical control sampler is simultaneously entered into a three-way mixer (ambient temperature: 25 C) through a polytetrafluoroethylene tube with an inner diameter of 1,000 mum and the second effluent. Then, under its own pressure, it enters a polytetrafluoroethylene tube with an internal diameter of 1000 mum at a set temperature control (80 C).The Suzuki coupling reaction between the second effluent product and 5-bromo-7-azaindole was completed within the set residence time t3 (1min), and the target product N-{2-chloro-5-[1H-pyrazolo(3,4-b)pyridin-5-yl]pyridin-3-yl}benzenesulfonamide. (4) The above effluent, the solvent was distilled off under reduced pressure, and then separated through a silica gel column by column chromatography (DCM / MeOH, 3: 1), and then the solvent was distilled off under reduced pressure to obtain the target product N-{2-chloro-5-[1H-pyrazolo(3,4-b)pyridin-5-yl]pyridin-3-yl}benzenesulfonamide, yield 84%, purity 98%.

Reference： [1]Patent: CN110498798,2019,A .Location in patent: Paragraph 0148-0149; 0152-0153

6
[ 22190-33-6 ]
[ 1083326-55-9 ]
N-(2-chloro-5-(indolin-5-yl)pyridin-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;	General Procedure for the Synthesis of Compounds 5-24. General procedure: To a 25mL three neck reaction bottle, H3 (0.2g, 0.51mmol, 1.0 equiv.), compounds M5 - M24 (1.05 equiv.), potassium carbonate (0.18g, 1.28mmol), PdCl2(dppf) (0.019g, 0.026mmol) in 1,4-dioxane (6.0mL), and H2O (1.5mL) were added. The reaction mixture was stirred at 100°C for 12h under a nitrogen atmosphere. After cooling to room temperature, the solution was adjusted to pH 5-6 with 1M hydrochloric acid, extracted with CH2Cl2 three times. The organic phase was washed with brine, dried over Na2SO4, and concentrated under vacuum and purified by silica gel column chromatography (EtOAc/petroleum ether, 1:5 to 1:1 or CH2Cl2/EtOAc, 10:1 to 1:1) to afford the pure product.

Reference： [1]Yang, Chengbin; Xu, Chenyue; Li, Zhipeng; Chen, Yi; Wu, Tianze; Hong, Hui; Lu, Mingzhu; Jia, Yu; Yang, Yongtai; Liu, Xiaofeng; Deng, Mingli; Chen, Zhenxia; Li, Qingquan; Ling, Yun; Zhou, Yaming [European Journal of Medicinal Chemistry, 2021, vol. 223]

7
[ 23145-07-5 ]
[ 1083326-55-9 ]
N-(5-(benzofuran-5-yl)-2-chloropyridin-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere;	General procedure: To a 25mL three neck reaction bottle, H3 (0.2g, 0.51mmol, 1.0 equiv.), compounds M5 - M24 (1.05 equiv.), potassium carbonate (0.18g, 1.28mmol), PdCl2(dppf) (0.019g, 0.026mmol) in 1,4-dioxane (6.0mL), and H2O (1.5mL) were added. The reaction mixture was stirred at 100C for 12h under a nitrogen atmosphere. After cooling to room temperature, the solution was adjusted to pH 5-6 with 1M hydrochloric acid, extracted with CH2Cl2 three times. The organic phase was washed with brine, dried over Na2SO4, and concentrated under vacuum and purified by silica gel column chromatography (EtOAc/petroleum ether, 1:5 to 1:1 or CH2Cl2/EtOAc, 10:1 to 1:1) to afford the pure product.

Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 223

8
[ 1083326-55-9 ]
[ 220957-39-1 ]
N-(2-chloro-5-(furo[2,3-b]pyridin-5-yl)pyridin-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;	General Procedure for the Synthesis of Compounds 5-24. General procedure: To a 25mL three neck reaction bottle, H3 (0.2g, 0.51mmol, 1.0 equiv.), compounds M5 - M24 (1.05 equiv.), potassium carbonate (0.18g, 1.28mmol), PdCl2(dppf) (0.019g, 0.026mmol) in 1,4-dioxane (6.0mL), and H2O (1.5mL) were added. The reaction mixture was stirred at 100°C for 12h under a nitrogen atmosphere. After cooling to room temperature, the solution was adjusted to pH 5-6 with 1M hydrochloric acid, extracted with CH2Cl2 three times. The organic phase was washed with brine, dried over Na2SO4, and concentrated under vacuum and purified by silica gel column chromatography (EtOAc/petroleum ether, 1:5 to 1:1 or CH2Cl2/EtOAc, 10:1 to 1:1) to afford the pure product.

9
[ 651780-02-8 ]
[ 1083326-55-9 ]
N-(2-chloro-5-(1H-indazol-5-yl)pyridin-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;	General Procedure for the Synthesis of Compounds 5-24. General procedure: To a 25mL three neck reaction bottle, H3 (0.2g, 0.51mmol, 1.0 equiv.), compounds M5 - M24 (1.05 equiv.), potassium carbonate (0.18g, 1.28mmol), PdCl2(dppf) (0.019g, 0.026mmol) in 1,4-dioxane (6.0mL), and H2O (1.5mL) were added. The reaction mixture was stirred at 100°C for 12h under a nitrogen atmosphere. After cooling to room temperature, the solution was adjusted to pH 5-6 with 1M hydrochloric acid, extracted with CH2Cl2 three times. The organic phase was washed with brine, dried over Na2SO4, and concentrated under vacuum and purified by silica gel column chromatography (EtOAc/petroleum ether, 1:5 to 1:1 or CH2Cl2/EtOAc, 10:1 to 1:1) to afford the pure product.

10
[ 1083326-55-9 ]
[ 876-88-0 ]
N-(2-chloro-5-(4-hydroxycinnolin-6-yl)pyridin-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water Inert atmosphere; Reflux;	N-(2-chloro-5-(4-morpholinocinnolin-6-yl)pyridin-3-yl)benzenesulfonamide General procedure: Synthesized following General Procedure C. Compound 39a (0.56 g, 1.4 mmol), compound 34a (0.38 g, 1.3 mmol), anhydrous K2CO3 (0.35 g, 2.5 mmol) solved in water (2 mL), PdCl2(dppf) (50 mg, 0.068 mmol) and 1,4-dioxane (15 mL) were stirred overnight at reflux under N2 atmosphere. Then the mixture was diluted with EA (30 mL) and purified by column chromatography to get 1 (0.25 g, 41%).

Reference： [1]Chen, Yi; Deng, Mingli; Jia, Yu; Ling, Yun; Liu, Xiaofeng; Lu, Mingzhu; Tian, Chengze; Wu, Tianze; Yang, Chengbin; Yang, Yongtai; Zhou, Yaming [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 48]

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P322
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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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H202	Explosive; severe projection hazard
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1083326-55-9 ] {[proInfo.proName]}

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[ 1083326-55-9 ] Synthesis Path-Downstream 1~10

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