[ CAS No. 90944-62-0 ] {[proInfo.proName]}

Name: 90944-62-0|4-Bromo-N,N-diethylbenzenesulfonamide|98%
Brand: Ambeed
SKU: A430935
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Quality Control of [ 90944-62-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 90944-62-0 ]

CAS No. :	90944-62-0	MDL No. :	MFCD00587586
Formula :	C₁₀H₁₄BrNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NRGTZJXYAAGKQJ-UHFFFAOYSA-N
M.W :	292.19	Pubchem ID :	347453
Synonyms :

Safety of [ 90944-62-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 90944-62-0 ]

* 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 [ 90944-62-0 ]
Downstream synthetic route of [ 90944-62-0 ]

[ 90944-62-0 ] Synthesis Path-Upstream 1~6

1
[ 90944-62-0 ]
[ 701-34-8 ]

Reference： [1] Synlett, 2004, # 11, p. 1901 - 1904

2
[ 109-89-7 ]
[ 98-58-8 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	at 20℃; for 12 h; Cooling with ice	4-Bromobenzenesulfonyl chloride (1.00g, 3.91 mmol) was dissolved in dichloromethane (30.00 ml), and cooled on ice. Diethylamine (1.19 ml, 11.54 mmol) was added to the mixture and stirred for 5 minutes, the ice was removed, and then the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was diluted with dichloromethane and washed with water and brine. An organic solvent layer was collected, dehydrated with anhydrous magnesium sulfate (MgSO₄), filtered, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Hex:EA=3:1), thereby obtaining 4-bromo-N,N-diethylbenzenesulfonamide (1.10 g, 96percent yield). ¹H NMR (CDCl₃, 500MHz) δ 7.67 (4H, m), 3.23 (4H, q, J = 7.0 Hz), 1.13 (6H, t)

Reference： [1] Patent: EP3327000, 2018, A1, . Location in patent: Paragraph 0102
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 21, p. 3878 - 3894
[3] Journal of the American Chemical Society, 1923, vol. 45, p. 2697
[4] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8274 - 8276
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6575 - 6577
[6] Patent: WO2010/55005, 2010, A1, . Location in patent: Page/Page column 82

3
[ 2297-64-5 ]
[ 109-89-7 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667 h;	General procedure: To a mixture of arylsulfonyl hydrazide 1 (0.5 mmol) and amine (0.75 mmol) was added TBHP (0.2 mL, 70percent wt/wt in H₂O, 2.0 mmol) followed by molecular iodine (0.025 g, 0.10 mmol, 20 molpercent) at room temperature. The reaction was completed after the addition of iodine within a minute. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with ethyl acetate, and quenched with saturated sodium thiosulphate solution and extracted twice with ethyl acetate (2 × 10 mL). The organic layer was washed with water and dried over anhyd. sodium sulphate. The solvent was evaporated in vacuo to afford pure sulfonamide derivative (8–12).

Reference： [1] Tetrahedron Letters, 2016, vol. 57, # 11, p. 1232 - 1235

4
[ 121-44-8 ]
[ 98-58-8 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With dipotassium hydrogenphosphate; oxygen; eosin y In water; acetonitrile at 20℃; Irradiation; Green chemistry	General procedure: To a 10 mL round bottom flask equipped with magnetic stirring bar was added4-toluenesulfonyl chloride 1a (0.2 mmol), triethylamine 2a (1 mmol), Eosin Y (3molpercent), K2HPO4 (1.5 eq) and CH3CN/H2O (1/1, 6 mL). The solution was irradiatedwith 12 W Blue LEDs at room temperature in O2 atmosphere. After the completion ofthe reaction (indicated by TLC), the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel withpetroleum ether/ethyl acetate (5:1) to afford the desired pure product 4a.

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 29, p. 7018 - 7023
[2] Synlett, 2017, vol. 28, # 13, p. 1630 - 1635

5
[ 34176-08-4 ]
[ 121-44-8 ]
[ 90944-62-0 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 13, p. 3194 - 3197

6
[ 150-77-6 ]
[ 98-58-8 ]
[ 90944-62-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 18, p. 3502 - 3506

[ 90944-62-0 ] Synthesis Path-Downstream 1~18

1
[ 109-89-7 ]
[ 98-58-8 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	In dichloromethane at 20℃; for 12h; Cooling with ice;	35.1 Step 1: Preparation of 4-bromo-N,N-diethylbenzenesulfonamide 4-Bromobenzenesulfonyl chloride (1.00g, 3.91 mmol) was dissolved in dichloromethane (30.00 ml), and cooled on ice. Diethylamine (1.19 ml, 11.54 mmol) was added to the mixture and stirred for 5 minutes, the ice was removed, and then the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was diluted with dichloromethane and washed with water and brine. An organic solvent layer was collected, dehydrated with anhydrous magnesium sulfate (MgSO4), filtered, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Hex:EA=3:1), thereby obtaining 4-bromo-N,N-diethylbenzenesulfonamide (1.10 g, 96% yield). 1H NMR (CDCl3, 500MHz) δ 7.67 (4H, m), 3.23 (4H, q, J = 7.0 Hz), 1.13 (6H, t)
91%	In dichloromethane at 0 - 25℃; for 12h;
83%	With triethylamine In dichloromethane at 20℃;	I 4-Bromo-N,N-diethylbenzenesulfonamide (2a). To a solution of diethylamine (730 mg, 10.0 mmol) and triethylamine (2.02 g, 20.0 mmol) was added 4-bromobenzenesulfonyl chloride (1a, 2.56 g, 10.0 mmol) portionwise. The mixture was stirred at room temperature overnight. The mixture was concentrated and purified with flash chromatography (10% EtOAc in hexane) to give 2a as a colorless oil. (2.44 g, 83%). 1H NMR (300 MHz, CDCl3) δ 7.73-7.62 (m, 4H), 3.26 (q, J = 7.1 Hz, 4H), 1.15 (t, J = 7.1 Hz, 6H). LC-MS (ESI) m/z 291.9, 293.9 [M + H]+.

83%	With triethylamine In dichloromethane at 20℃;	I 4-Bromo-N,N-diethylbenzenesulfonamide (2a). To a solution of diethylamine (730 mg, 10.0 mmol) and triethylamine (2.02 g, 20.0 mmol) was added 4-bromobenzenesulfonyl chloride (1a, 2.56 g, 10.0 mmol) portionwise. The mixture was stirred at room temperature overnight. The mixture was concentrated and purified with flash chromatography (10% EtOAc in hexane) to give 2a as a colorless oil. (2.44 g, 83%). 1H NMR (300 MHz, CDCl3) δ 7.73-7.62 (m, 4H), 3.26 (q, J = 7.1 Hz, 4H), 1.15 (t, J = 7.1 Hz, 6H). LC-MS (ESI) m/z 291.9, 293.9 [M + H]+.
83%	With triethylamine In dichloromethane at 20℃;
83%	With triethylamine In dichloromethane at 20℃;	I 4-Bromo-N,N-diethylbenzenesulfonamide (2a). To a solution of diethylamine (730 mg, 10.0 mmol) and triethylamine (2.02 g, 20.0 mmol) was added 4-bromobenzenesulfonyl chloride (1a, 2.56 g, 10.0 mmol) portionwise. The mixture was stirred at room temperature overnight. The mixture was concentrated and purified with flash chromatography (10% EtOAc in hexane) to give 2a as a colorless oil. (2.44 g, 83%). 1H NMR (300 MHz, CDCl3) δ 7.73-7.62 (m, 4H), 3.26 (q, J = 7.1 Hz, 4H), 1.15 (t, J = 7.1 Hz, 6H). LC-MS (ESI) m/z 291.9, 293.9 [M + H]+.
282 mg	In tetrahydrofuran for 3h;
	In dichloromethane at 23℃;
	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;	Diisopropylethylamine (10.47 ml_, 58.79 mmol) was added at 0 °C to a stirred solution of diethyl amine (1.7 g, 23.5 mmol) in tetrahydrofuran (50 ml_) and the reaction mixture was stirred at room temperature for 15 minutes. A 0.1 M solution of 4-bromo-benzenesulfonyl chloride (6.01 g, 23.5 mmol) in tetrahydrofuran was added at room temperature and the reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated off under reduced pressure. The residue was diluted with ethyl acetate, and the inorganic salts were filtered through a celite bed. The filtrate was washed with 2 N aqueous HCI, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 1-bromo-4-Λ/,/V,- diethylbenzenesulfonamide, which was used in subsequent reactions without further purification. MS cald. for C10H14BrNO2S [M+] 292, obsd 293.

Reference： [1]Current Patent Assignee: DONGGUK UNIVERSITY; KOREA UNIVERSITY - EP3327000, 2018, A1 Location in patent: Paragraph 0102
[2]Plobeck; Delorme; Wei; Yang; Zhou; Schwarz; Gawell; Gagnon; Pelcman; Schmidt; Yue; Walpole; Brown; Zhou; Labare; Payza; St-Ogne; Kamassah; Morin; Projean; Ducharme; Roberts [Journal of Medicinal Chemistry, 2000, vol. 43, # 21, p. 3878 - 3894]
[3]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 63
[4]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 63
[5]Xue, Ding; Xu, Yibin; Kyani, Armita; Roy, Joyeeta; Dai, Lipeng; Sun, Duxin; Neamati, Nouri [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 343 - 368] Xue, Ding; Xu, Yibin; Kyani, Armita; Roy, Joyeeta; Dai, Lipeng; Sun, Duxin; Neamati, Nouri [Journal of Medicinal Chemistry, 2022, vol. 65, # 4, p. 3404 - 3419]
[6]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 61; 63
[7]Marvel; Smith [Journal of the American Chemical Society, 1923, vol. 45, p. 2697]
[8]Pandya, Rina; Murashima, Takashi; Tedeschi, Livio; Barrett, Anthony G. M. [Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8274 - 8276]
[9]Location in patent: scheme or table Shim, Jaechul; Eid, Clark; Lee, Julie; Liu, Erica; Chaudhary, Divya; Boschelli, Diane H. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6575 - 6577]
[10]Current Patent Assignee: ROCHE HOLDING AG - WO2010/55005, 2010, A1 Location in patent: Page/Page column 82

2
[ 90944-62-0 ]
[ 100-52-7 ]
[ 308110-14-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: N,N-diethyl-4-bromobenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane for 1h; Further stages.;

Reference： [1]Plobeck; Delorme; Wei; Yang; Zhou; Schwarz; Gawell; Gagnon; Pelcman; Schmidt; Yue; Walpole; Brown; Zhou; Labare; Payza; St-Ogne; Kamassah; Morin; Projean; Ducharme; Roberts [Journal of Medicinal Chemistry, 2000, vol. 43, # 21, p. 3878 - 3894]

3
[ 90944-62-0 ]
[ 93296-09-4 ]
[ 680183-40-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran Heating;

Reference： [1]Milburn, Robert R.; Snieckus, Victor [Angewandte Chemie - International Edition, 2004, vol. 43, # 7, p. 888 - 891]

4
[ 90944-62-0 ]
[ 701-34-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With chromium(III) acetate hydroxide; periodic acid In acetonitrile at 20℃; for 20h;

Reference： [1]Xu, Liang; Zhang, Suhong; Trudell, Mark L. [Synlett, 2004, # 11, p. 1901 - 1904]

5
[ 96-43-5 ]
[ 90944-62-0 ]
[ 1454889-57-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique; regioselective reaction;

Reference： [1]Bheeter, Charles Beromeo; Jin, Rongwei; Bera, Jitendra K.; Doucet, Henri [RSC Advances, 2013, vol. 3, # 17, p. 5987 - 5996]

6
[ 1192-58-1 ]
[ 90944-62-0 ]
[ 1454889-58-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique; regioselective reaction;

Reference： [1]Bheeter, Charles Beromeo; Jin, Rongwei; Bera, Jitendra K.; Doucet, Henri [RSC Advances, 2013, vol. 3, # 17, p. 5987 - 5996]

7
[ 300-87-8 ]
[ 90944-62-0 ]
[ 1358539-63-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique; regioselective reaction;

Reference： [1]Bheeter, Charles Beromeo; Jin, Rongwei; Bera, Jitendra K.; Doucet, Henri [RSC Advances, 2013, vol. 3, # 17, p. 5987 - 5996]

8
[ 1455-20-5 ]
[ 90944-62-0 ]
N,N-diethyl-4-(5-n-butylthiophen-2-yl)benzenesulfonamide [ No CAS ]

Reference： [1]RSC Advances,2013,vol. 3,p. 5987 - 5996

9
[ 90944-62-0 ]
[ 18640-74-9 ]
N,N-diethyl-4-(2-isobutylthiazol-5-yl)benzenesulfonamide [ No CAS ]

Reference： [1]RSC Advances,2013,vol. 3,p. 5987 - 5996

10
[ 90944-62-0 ]
[ 167156-20-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium iodide In 1,4-dioxane; dichloromethane at 180℃; for 0.5h; Flow reactor; Inert atmosphere;

Reference： [1]Chen, Mao; Ichikawa, Saki; Buchwald, Stephen L. [Angewandte Chemie - International Edition, 2015, vol. 54, # 1, p. 263 - 266][Angew. Chem., 2015, vol. 127, # 01, p. 265 - 268,4]

11
[ 2297-64-5 ]
[ 109-89-7 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667h;	General procedure for the synthesis of sulfonamides 8-12 General procedure: To a mixture of arylsulfonyl hydrazide 1 (0.5 mmol) and amine (0.75 mmol) was added TBHP (0.2 mL, 70% wt/wt in H2O, 2.0 mmol) followed by molecular iodine (0.025 g, 0.10 mmol, 20 mol%) at room temperature. The reaction was completed after the addition of iodine within a minute. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with ethyl acetate, and quenched with saturated sodium thiosulphate solution and extracted twice with ethyl acetate (2 × 10 mL). The organic layer was washed with water and dried over anhyd. sodium sulphate. The solvent was evaporated in vacuo to afford pure sulfonamide derivative (8-12).

Reference： [1]Parumala, Santosh Kumar Reddy; Peddinti, Rama Krishna [Tetrahedron Letters, 2016, vol. 57, # 11, p. 1232 - 1235]

12
[ 121-44-8 ]
[ 98-58-8 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(I) oxide; oxygen In 1,2-dichloro-ethane at 50℃; for 4h; Sealed tube;
68%	With dipotassium hydrogenphosphate; oxygen; eosin y In water; acetonitrile at 20℃; Irradiation; Green chemistry;	General procedure for the synthesis of sulfonamides General procedure: To a 10 mL round bottom flask equipped with magnetic stirring bar was added4-toluenesulfonyl chloride 1a (0.2 mmol), triethylamine 2a (1 mmol), Eosin Y (3mol%), K2HPO4 (1.5 eq) and CH3CN/H2O (1/1, 6 mL). The solution was irradiatedwith 12 W Blue LEDs at room temperature in O2 atmosphere. After the completion ofthe reaction (indicated by TLC), the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel withpetroleum ether/ethyl acetate (5:1) to afford the desired pure product 4a.

Reference： [1]Ji, Jing; Liu, Zhengyi; Liu, Ping; Sun, Peipei [Organic and Biomolecular Chemistry, 2016, vol. 14, # 29, p. 7018 - 7023]
[2]Cai, Yuguo; Zhang, Ronghua; Sun, Deli; Xu, Song; Zhou, Qiguang [Synlett, 2017, vol. 28, # 13, p. 1630 - 1635]

13
[ CAS Unavailable ]
[ 121-44-8 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tert.-butylhydroperoxide; iodine In water at 80℃; for 8h; Sealed tube;

Reference： [1]Lai, Junyi; Chang, Liming; Yuan, Gaoqing [Organic Letters, 2016, vol. 18, # 13, p. 3194 - 3197]

14
[ 90944-62-0 ]
[ CAS Unavailable ]
[ 1178333-50-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 17h;	35.2 Step 2: Preparation of N,N-diethyl-4-(3-hydroxyprop-1-ynyl)benzenesulfonamide The 4-bromo-N,N-diethylbenzenesulfonamide (500.00 mg, 1.71 mmol) obtained in Step 1 and propargyl alcohol (0.20 ml, 3.42 mmol) were dissolved in triethylamine (10.00 ml), and stirred for 5 minutes. Bis(triphenylphosphine)palladium (II) dichloride (119.32 mg, 0.17 mmol) and copper iodide (I)(32.37 mg, 0.17 mmol) were added to the mixture, heated at 60 °C, refluxed, and stirred for 17 hours. The reaction solution was cooled at room temperature and concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate and washed with water and brine. An organic solvent layer was collected, dehydrated with anhydrous magnesium sulfate (MgSO4), filtered, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Hex:EA=1:1), thereby obtaining N,N-diethyl-4-(3-hydroxyprop-1-ynyl)benzenesulfonamide (286.00 mg, 63% yield). 1H NMR (CDCl3, 500MHz) δ 7.66 (2H, d, J = 8.0 Hz), 7.42 (2H, d, J = 8.0 Hz), 4.44 (2H, s), 3.16 (4H, q, J = 7.0 Hz), 1.05 (6H, t).

Reference： [1]Current Patent Assignee: DONGGUK UNIVERSITY; KOREA UNIVERSITY - EP3327000, 2018, A1 Location in patent: Paragraph 0103

15
[ 150-77-6 ]
[ 98-58-8 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With calcium hydride In acetonitrile at 90℃; for 1h; Inert atmosphere; Schlenk technique; regiospecific reaction;

Reference： [1]Fu, Ying; Xu, Qin-Shan; Shi, Chun-Zhao; Du, Zhengyin; Xiao, Caiqin [Advanced Synthesis and Catalysis, 2018, vol. 360, # 18, p. 3502 - 3506]

16
[ CAS Unavailable ]
[ 109-89-7 ]
[ 90944-62-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With ethylene dibromide; sodium iodide In water at 60℃; for 8h; Schlenk technique; Green chemistry;

Reference： [1]Fu, Ying; Li, Quan-Zhou; Xu, Qin-Shan; Hügel, Helmut; Li, Ming-Peng; Du, Zhengyin [European Journal of Organic Chemistry, 2018, vol. 2018, # 48, p. 6966 - 6970]

17
[ 90944-62-0 ]
[ 100-53-8 ]
[ 2749555-73-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane Reflux; Inert atmosphere;	I 4-(Benzylthio)-N,N-diethylbenzenesulfonamide (3a). A solution of 2a, DIEA in dioxane was degassed and flushed with argon for three times. Then Pd2(dba)3, XantPhos, and benzyl mercaptan was added subsequently. Then it was degassed and flushed with argon for three times again before it was heated at reflux overnight. The mixture was cooled and the needle-like crystals generated was filtered off. The filtrate was concentrated and purified with flash chromatography (20% EtOAc in hexane) to give 3a as a yellow solid (520 mg, 91%). 1H NMR (300 MHz, CDCl3) δ 7.68 (d, J = 8.1 Hz, 2H), 7.43-7.22 (m, 7H), 4.22 (s, 2H), 3.23 (q, J = 7.2 Hz, 4H), 1.13 (t, J = 7.2 Hz, 6H). LC-MS (ESI) m/z 336.0 [M + H]+.
91%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane Reflux; Inert atmosphere;	I 4-(Benzylthio)-N,N-diethylbenzenesulfonamide (3a). A solution of 2a, DIEA in dioxane was degassed and flushed with argon for three times. Then Pd2(dba)3, XantPhos, and benzyl mercaptan was added subsequently. Then it was degassed and flushed with argon for three times again before it was heated at reflux overnight. The mixture was cooled and the needle-like crystals generated was filtered off. The filtrate was concentrated and purified with flash chromatography (20% EtOAc in hexane) to give 3a as a yellow solid (520 mg, 91%). 1H NMR (300 MHz, CDCl3) δ 7.68 (d, J = 8.1 Hz, 2H), 7.43-7.22 (m, 7H), 4.22 (s, 2H), 3.23 (q, J = 7.2 Hz, 4H), 1.13 (t, J = 7.2 Hz, 6H). LC-MS (ESI) m/z 336.0 [M + H]+.
91%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane Inert atmosphere; Reflux;

91%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane Reflux; Inert atmosphere;
91%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane Reflux; Inert atmosphere;	I 4-(Benzylthio)-N,N-diethylbenzenesulfonamide (3a). A solution of 2a, DIEA in dioxane was degassed and flushed with argon for three times. Then Pd2(dba)3, XantPhos, and benzyl mercaptan was added subsequently. Then it was degassed and flushed with argon for three times again before it was heated at reflux overnight. The mixture was cooled and the needle-like crystals generated was filtered off. The filtrate was concentrated and purified with flash chromatography (20% EtOAc in hexane) to give 3a as a yellow solid (520 mg, 91%). 1H NMR (300 MHz, CDCl3) δ 7.68 (d, J = 8.1 Hz, 2H), 7.43-7.22 (m, 7H), 4.22 (s, 2H), 3.23 (q, J = 7.2 Hz, 4H), 1.13 (t, J = 7.2 Hz, 6H). LC-MS (ESI) m/z 336.0 [M + H]+.

Reference： [1]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 63
[2]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 63
[3]Xue, Ding; Xu, Yibin; Kyani, Armita; Roy, Joyeeta; Dai, Lipeng; Sun, Duxin; Neamati, Nouri [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 343 - 368]
[4]Xue, Ding; Xu, Yibin; Kyani, Armita; Roy, Joyeeta; Dai, Lipeng; Sun, Duxin; Neamati, Nouri [Journal of Medicinal Chemistry, 2022, vol. 65, # 4, p. 3404 - 3419]
[5]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 61; 63

18
[ 90944-62-0 ]
[ 25137-01-3 ]
[ 2749554-99-0 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: N,N-diethyl-4-bromobenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With N-sulfinyltriphenylmethylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #3: (R)-ethyl nipecotate Further stages;	I Ethyl (3R)-1-(4-(N,N-diethylsulfamoyl)phenylsulfonimidoyl)piperidine-3-carboxylate (DX2-225). To a solution of 2a (100 mg, 0.34 mmol) in THF (4 mL) was added nBuLi (0.14 mL, 0.34 mmol, 2.5 M in hexane) dropwise and the mixture was stirred at the same temperature for 1h. N- Sulfinyltriphenylmethylamine (104 mg, 0.34 mmol) was then added as a THF solution dropwise and the mixture was stirred at the same temperature for 25 min before warmed to 0°C in an ice bath. After stirred for 5 min, tBuOCl (39 mg, 0.36 mmol) was added in a darkened hood with aluminum foil covering the flask and stirred for 25 min. Then ethyl (R)-piperidine-3-carboxylate (80 mg, 0.51 mmol) and Et3N (34 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature overnight and quenched with MsOH (326 mg, 3.40 mmol), diluted with DCM, washed with sat.aq. NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with preparative HPLC to give DX2-225 as a white solid (57 mg, 39%). 1H NMR (300 MHz, CDCl3) δ 8.20 (dd, J = 6.0, 3.4 Hz, 1H), 8.05 (dd, J = 5.9, 3.5 Hz, 1H), 7.68 (dd, J = 5.9, 3.4 Hz, 2H), 4.13 (q, J = 7.1 Hz, 2H), 3.95 (d, J = 13.9 Hz, 1H), 3.83 (d, J = 13.4 Hz, 1H), 3.53-3.34 (m, 4H), 2.98 (dd, J = 13.0, 10.6 Hz, 1H), 2.91-2.80 (m, 1H), 2.72-2.61 (m, 1H), 2.22-2.03 (m, 1H), 1.85-1.47 (m, 3H), 1.25 (t, J = 7.1 Hz, 3H), 1.18 (t, J = 7.1 Hz, 6H). LC-MS (ESI) m/z 432.0 [M + H]+.
39%	Stage #1: N,N-diethyl-4-bromobenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With N-sulfinyltriphenylmethylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #3: (R)-ethyl nipecotate Further stages;	I Ethyl (3R)-1-(4-(N,N-diethylsulfamoyl)phenylsulfonimidoyl)piperidine-3-carboxylate (DX2-225). To a solution of 2a (100 mg, 0.34 mmol) in THF (4 mL) was added nBuLi (0.14 mL, 0.34 mmol, 2.5 M in hexane) dropwise and the mixture was stirred at the same temperature for 1h. N- Sulfinyltriphenylmethylamine (104 mg, 0.34 mmol) was then added as a THF solution dropwise and the mixture was stirred at the same temperature for 25 min before warmed to 0°C in an ice bath. After stirred for 5 min, tBuOCl (39 mg, 0.36 mmol) was added in a darkened hood with aluminum foil covering the flask and stirred for 25 min. Then ethyl (R)-piperidine-3-carboxylate (80 mg, 0.51 mmol) and Et3N (34 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature overnight and quenched with MsOH (326 mg, 3.40 mmol), diluted with DCM, washed with sat.aq. NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with preparative HPLC to give DX2-225 as a white solid (57 mg, 39%). 1H NMR (300 MHz, CDCl3) δ 8.20 (dd, J = 6.0, 3.4 Hz, 1H), 8.05 (dd, J = 5.9, 3.5 Hz, 1H), 7.68 (dd, J = 5.9, 3.4 Hz, 2H), 4.13 (q, J = 7.1 Hz, 2H), 3.95 (d, J = 13.9 Hz, 1H), 3.83 (d, J = 13.4 Hz, 1H), 3.53-3.34 (m, 4H), 2.98 (dd, J = 13.0, 10.6 Hz, 1H), 2.91-2.80 (m, 1H), 2.72-2.61 (m, 1H), 2.22-2.03 (m, 1H), 1.85-1.47 (m, 3H), 1.25 (t, J = 7.1 Hz, 3H), 1.18 (t, J = 7.1 Hz, 6H). LC-MS (ESI) m/z 432.0 [M + H]+.
39%	Stage #1: N,N-diethyl-4-bromobenzenesulfonamide With n-butyllithium; hypochlorous acid tert-butyl ester; N-sulfinyltriphenylmethylamine In tetrahydrofuran at -78 - 0℃; for 1.83333h; Stage #2: (R)-ethyl nipecotate With triethylamine In tetrahydrofuran at 20℃;

39%

Stage #1: N,N-diethyl-4-bromobenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With N-sulfinyltriphenylmethylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #3: (R)-ethyl nipecotate Further stages;

I Ethyl (3R)-1-(4-(N,N-diethylsulfamoyl)phenylsulfonimidoyl)piperidine-3-carboxylate (DX2-225). To a solution of 2a (100 mg, 0.34 mmol) in THF (4 mL) was added nBuLi (0.14 mL, 0.34 mmol, 2.5 M in hexane) dropwise and the mixture was stirred at the same temperature for 1h. N- Sulfinyltriphenylmethylamine (104 mg, 0.34 mmol) was then added as a THF solution dropwise and the mixture was stirred at the same temperature for 25 min before warmed to 0°C in an ice bath. After stirred for 5 min, tBuOCl (39 mg, 0.36 mmol) was added in a darkened hood with aluminum foil covering the flask and stirred for 25 min. Then ethyl (R)-piperidine-3-carboxylate (80 mg, 0.51 mmol) and Et3N (34 mg, 0.34 mmol) was added, and the mixture was stirred at room temperature overnight and quenched with MsOH (326 mg, 3.40 mmol), diluted with DCM, washed with sat.aq. NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with preparative HPLC to give DX2-225 as a white solid (57 mg, 39%). 1H NMR (300 MHz, CDCl3) δ 8.20 (dd, J = 6.0, 3.4 Hz, 1H), 8.05 (dd, J = 5.9, 3.5 Hz, 1H), 7.68 (dd, J = 5.9, 3.4 Hz, 2H), 4.13 (q, J = 7.1 Hz, 2H), 3.95 (d, J = 13.9 Hz, 1H), 3.83 (d, J = 13.4 Hz, 1H), 3.53-3.34 (m, 4H), 2.98 (dd, J = 13.0, 10.6 Hz, 1H), 2.91-2.80 (m, 1H), 2.72-2.61 (m, 1H), 2.22-2.03 (m, 1H), 1.85-1.47 (m, 3H), 1.25 (t, J = 7.1 Hz, 3H), 1.18 (t, J = 7.1 Hz, 6H). LC-MS (ESI) m/z 432.0 [M + H]+.

Reference： [1]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 102-103
[2]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 102-103
[3]Xue, Ding; Xu, Yibin; Kyani, Armita; Roy, Joyeeta; Dai, Lipeng; Sun, Duxin; Neamati, Nouri [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 343 - 368]
[4]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2021/242753, 2021, A1 Location in patent: Page/Page column 61; 102-103

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P401
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
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
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H370	Causes damage to organs
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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. 90944-62-0 ] {[proInfo.proName]}

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[ 90944-62-0 ] Synthesis Path-Upstream 1~6

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