Name: 220227-84-9|3-(Trifluoromethoxy)benzene-1-sulfonyl chloride|98%
Brand: Ambeed
SKU: A756379
Price: 14.0 USD
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1
[ 220227-84-9 ]
[ 686717-51-1 ]
N-{3-[4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-yl]-phenyl}-3-trifluoromethoxy-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Wu, Baogen; Kuhen, Kelli; Ngoc Nguyen, Truc; Ellis, David; Anaclerio, Beth; He, Xiaohui; Yang, Kunyong; Karanewsky, Donald; Yin, Hong; Wolff, Karen; Bieza, Kimberly; Caldwell, Jeremy; He, Yun [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3430 - 3433]

2
[ 220227-84-9 ]
[ 562075-34-7 ]
2-(3-trifluoromethoxy-benzenesulfonylimino)-imidazolidine-1-carbodithioic acid 3-thioxo-5,6-dihydro-imidazo[2,1-c][1,2,4]thiadiazol-7-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With pyridine at 20℃; for 12h;

Reference： [1]Saczewski, Jaroslaw; Brzozowski, Zdzialaw; Saczewski, Franciszek; Bednarski, Patrick J.; Liebeke, Manuel; Gdaniec, Maria [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 14, p. 3663 - 3667]

3
[ 220227-84-9 ]
[ 578-54-1 ]
[ 120-20-7 ]
[ 79-08-3 ]
N-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-[(2-ethyl-phenyl)-(3-trifluoromethoxy-benzenesulfonyl)-amino]-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]McKeown, Stephen C.; Hall, Adrian; Blunt, Richard; Brown, Susan H.; Chessell, Iain P.; Chowdhury, Anita; Giblin, Gerard M.P.; Healy, Mark P.; Johnson, Matthew R.; Lorthioir, Olivier; Michel, Anton D.; Naylor, Alan; Lewell, Xiao; Roman, Shilina; Watson, Stephen P.; Winchester, Wendy J.; Wilson, Richard J. [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1750 - 1754]

4
[ 220227-84-9 ]
[ 883901-38-0 ]
N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 20℃; for 15h;	II.1.7 1.7 3-Trifluoromethoxy-N-[4-((S)-1 -propyl-pyrrolidin-3-yl)-phenyl]- benzenesulfonamide and its hydrochloride0.4 g of (S )-3-(4-amino-phenyl)-1 -propyl-pyrrolidine (1.96 mmol) and 0.455 g of commercially available 3-trifluoromethoxy-phenylsulfonyl chloride (1.86 mmol) were dissolved in 15 ml of tetrahydrofuran. 0.82 ml of triethylamine (5.87 mmol) were added and the reaction mixture stirred for 15 h at room temperature. The solvents were evaporated under reduced pressure, the residue treated with water and adjusted to an alkaline pH with sodium hydroxide solution. The aqueous layer was extracted three times with diethyl ether, the organic layers combined, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified with silica gel chromatography with ethyl acetate/methanol (2.5-3%) as eluent, yielding 0.225 g of the purified product.ESI-MS: 429.15 [M+H] + 1H-NMR (CDCI3, 400 MHz): δ [ppm] 7.7 (d, 1 H), 7.55 (s, 1 H), 7.5 (t, 1 H), 7.4 (d, 1 H), 7.15 (d, 2H), 6.95 (d, 2H), 5.3 (bs, 1 H), 3.3 (m, 1 H), 3.05 (m, 1 H), 2.85 (m, 1 H), 2.65 (m, 1 H), 2.5 (m, 1 H), 2.45 (m, 2H), 2.3 (m, 1 H), 1.8 (m, 1 H), 1.55 (m, 2H), 0.9 (t, 3H).This material was dissolved in 15 ml of diethyl ether and 1 ml of dichloromethane, 0.61 ml of 1 N HCI in diethyl ether added, and after formation of a precipitate, the suspension evaporated under reduced pressure to yield 0.235 g of a white precipitate.

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2007/118899, 2007, A1 Location in patent: Page/Page column 145-146

5
[ 220227-84-9 ]
[ 954376-45-5 ]
N-[3-((S)-1-benzyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 20℃; for 16h;	II.7.2 7.2 N-[3-((S)-1 -Benzyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzene sulfonamide(S)-1-Benzyl-3-(3-amino-phenyl)-pyrrolidine (0.4 g, 1.59 mmol) and commercially available 3-trifluoromethoxy-benzene sulfonylchloride (0.39 g, 1.5 mmol) were dissolved in 30 ml tetrahydrofurane. 0.66 ml of triethylamine (3.75 mmol) were added and the mixture was stirred for 16 h at room temperature. The solvent was evaporated under reduced pressure and the residue was treated with water/diethylether. After adjusting the aqueous phase to alkaline pH with 1 N aqueous NaOH, the aqueous layer was extracted with diethylether and the combined organic layers dried over magnesium sulfate, filtered and evaporated. The product was purified via silica gel chromatography using an lsco Companion semi-automated chromatography system to yield 0.512 g of the desired compound.ESI-MS: 477.1 [M+H] +

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2007/118899, 2007, A1 Location in patent: Page/Page column 148

Yield	Reaction Conditions	Operation in experiment
		The following sulfonyl chlorides may be substituted for benzenesulfonyl chloride of Step One: ... 4-(Trifluoromethyl)benzenesulfonyl chloride 2-(Trifluoromethoxy)benzenesulfonyl chloride 3-(Trifluoromethoxy)benzenesulfonyl chloride 4-(Trifluoromethoxy)benzenesulfonyl chloride ...

7
[ 220227-84-9 ]
7-aminobenzimidazole dihydrochloride [ No CAS ]
[ 727658-28-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine at 100℃; for 3h;

Reference： [1]Elkin; Tolkacheva; Chernysheva; Karmanova; Konyushkin; Semenov [Russian Chemical Bulletin, 2007, vol. 56, # 6, p. 1216 - 1226]

8
[ 220227-84-9 ]
[ 106-50-3 ]
[ 1030598-40-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 25 - 28℃;

Reference： [1]Jain, Mukul R.; Shetty, Shankar; Chakrabarti, Ganes; Pandya, Vrajesh; Sharma, Ajay; Parmar, Bhavesh; Srivastava, Soma; Raviya, Mehul; Soni, Hitesh; Patel, Pankaj R. [European Journal of Medicinal Chemistry, 2008, vol. 43, # 4, p. 880 - 884]

9
[ 220227-84-9 ]
[ 850796-94-0 ]
[ 850796-95-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	8.B This material was then dissolved in dichloromethane (5 mL) and cooled with an ice/water bath. The mixture was treated with 3-trifluoromethoxybenzenesulfonyl chloride (125 mg, 0.48 mmol) and diisopropylethylamine and allowed to stir and warm to room temperature overnight. The reaction was then diluted with dichloromethane, extracted with water once, dried over Na2S 04, filtered and the solvent was removed. The resulting oil was purified over silica gel using a linear gradient of 0-80% ethyl acetate in hexane to afford 214 mg (87%) of (3S)- [3-Cyclopentyl- (2S)- (3-trifluoromethoxy-benzenesulfonylamino)- propionylamino]-4-hydroxy-butyric acid tert-butyl ester

Reference： [1]Current Patent Assignee: IRM LLC - WO2005/39496, 2005, A2 Location in patent: Page/Page column 52

10
[ 220227-84-9 ]
[ 232941-00-3 ]
[ 1161341-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 20℃;

Reference： [1]Location in patent: experimental part Johnson, Sherida L.; Chen, Li-Hsing; Barile, Elisa; Emdadi, Aras; Sabet, Mojgan; Yuan, Hongbin; Wei, Jun; Guiney, Donald; Pellecchia, Maurizio [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 9, p. 3352 - 3368]

11
[ 220227-84-9 ]
[ 99-92-3 ]
[ 1016063-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 60℃; for 1h;

Reference： [1]Location in patent: scheme or table Wash, Paul L.; Hoffman, Timothy Z.; Wiley, Brandon M.; Bonnefous, Celine; Smith, Nicholas D.; Sertic, Michael S.; Lawrence, Charles M.; Symons, Kent T.; Nguyen, Phan-Manh; Lustig, Kevin D.; Guo, Xin; Annable, Tami; Noble, Stewart A.; Hager, Jeffrey H.; Hassig, Christian A.; Malecha, James W. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 24, p. 6482 - 6485]

12
[ 220227-84-9 ]
[ 1635-61-6 ]
[ 1221884-26-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride In 1,4-dioxane at 0℃; for 0.5h;

Reference： [1]Location in patent: experimental part Monforte, Anna-Maria; Logoteta, Patrizia; Luca, Laura De; Iraci, Nunzio; Ferro, Stefania; Maga, Giovanni; De Clercq, Erik; Pannecouque, Christophe; Chimirri, Alba [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 4, p. 1702 - 1710]

13
[ 220227-84-9 ]
[ 956488-93-0 ]
N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)-3-(trifluoromethoxy)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51 mg	With pyridine at 20℃; for 20h;

Reference： [1]Location in patent: experimental part Nourry, Arnaud; Zambon, Alfonso; Davies, Lawrence; Niculescu-Duvaz, Ion; Dijkstra, Harmen P.; Ménard, Delphine; Gaulon, Catherine; Niculescu-Duvaz, Dan; Suijkerbuijk, Bart M. J. M.; Manne, Frank Friedlos Helen A.; Kirk, Ruth; Whittaker, Steven; Marais, Richard; Springer, Caroline J. [Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1964 - 1978]

14
[ 220227-84-9 ]
[ 1072-97-5 ]
[ 1227721-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃;	8.1 3-(Trifluoromethoxy)benzene-l-sulfonyl chloride (Ig, 3.8mmol), 5-bromopyridin-2-amine (1.2eq, 0.8g, 4.6mmol) and triethylamine (2eq, 0.77g, 7.6mmol) were stirred together in dry DCM (20ml) at 00C for 5 minutes. The mixture was then warmed to room temperature, and stirred overnight. The mixture was diluted with DCM, washed with 2MNaOH (x2). The DCM layer was dried (MgSO4) and concentrated. The crude was purified by column chromatography eluting using a gradient (EtOAc/hexanes 1 :9 v/v). LCMS RT=2.15min, MH+= 397.1. 1H NMR (d6-DMSO): 11.56 (IH, br s), 8.33 (IH, s), 7.92 (2H, m),7.86 (IH, s), 7.77-7.67 (2H, m), 7.03 (IH, d, J 8.9).

Reference： [1]Current Patent Assignee: SUMMIT THERAPEUTICS PLC; BIOMARIN IGA LTD - WO2010/57833, 2010, A1 Location in patent: Page/Page column 91

15
[ 220227-84-9 ]
[ 1229096-85-8 ]
[ 1229096-93-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	With pyridine at 20℃;

Reference： [1]Location in patent: experimental part Yates, Christopher M.; Brown, Peter J.; Stewart, Eugene L.; Patten, Christopher; Austin, Robert J. H.; Holt, Jason A.; Maglich, Jodi M.; Angell, Davina C.; Sasse, Rosemary Z.; Taylor, Simon J.; Uings, Iain J.; Trump, Ryan P. [Journal of Medicinal Chemistry, 2010, vol. 53, # 11, p. 4531 - 4544]

16
[ 220227-84-9 ]
[ 578-66-5 ]
[ 1232007-27-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With pyridine at 130℃; for 0.05h; Microwave irradiation; Inert atmosphere;

Reference： [1]Rouffet, Matthieu; De Oliveira, Cesar Augusto F.; Udi, Yael; Agrawal, Arpita; Sagi, Irit; McCammon, J. Andrew; Cohen, Seth M. [Journal of the American Chemical Society, 2010, vol. 132, # 24, p. 8232 - 8233]

17
[ 220227-84-9 ]
[ 5805-39-0 ]
[ 1232007-91-8 ]

Yield	Reaction Conditions	Operation in experiment
58%	With pyridine at 130℃; for 0.05h; Microwave irradiation; Inert atmosphere;

Reference： [1]Rouffet, Matthieu; De Oliveira, Cesar Augusto F.; Udi, Yael; Agrawal, Arpita; Sagi, Irit; McCammon, J. Andrew; Cohen, Seth M. [Journal of the American Chemical Society, 2010, vol. 132, # 24, p. 8232 - 8233]

18
[ 220227-84-9 ]
[ 1225198-23-1 ]
[ 1225198-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 20℃; for 18h;	Preparation of Compound C0005 To a solution of compound 3-29 (145 mg, 0.4 mmol) in pyridine (2 mL) was added 3-trifluoro-methoxybenzenesulfonyl chloride (103 mg, 1.1 mmol). The mixture was then stirred at room temperature overnight (about 18 hours). Water was added then the mixture was extracted with DCM 3 times. The combined organic phase was washed with 3M HCl and concentrated to get the crude product. The crude product was purified to afford 40 mg of the desired product as white solid (1H NMR and LC-MS confirmed, HPLC 94.4%, yield).

Reference： [1]Current Patent Assignee: PAIN THERAPEUTICS INC - US2010/280057, 2010, A1 Location in patent: Page/Page column 22

19
[ 220227-84-9 ]
[ 1311151-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 20 °C 2: methanol; palladium 10% on activated carbon / dichloromethane

Reference： [1]Gentles, Robert G.; Ding, Min; Zheng, Xiaofan; Chupak, Louis; Poss, Michael A.; Beno, Brett R.; Pelosi, Lenore; Liu, Mengping; Lemm, Julie; Wang, Ying-Kai; Roberts, Susan; Gao, Min; Kadow, John [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3142 - 3147]

20
[ 220227-84-9 ]
[ 1311149-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 20 °C 2: methanol; palladium 10% on activated carbon / dichloromethane 3: butan-1-ol / 175 °C / Microwave irradiation

Reference： [1]Gentles, Robert G.; Ding, Min; Zheng, Xiaofan; Chupak, Louis; Poss, Michael A.; Beno, Brett R.; Pelosi, Lenore; Liu, Mengping; Lemm, Julie; Wang, Ying-Kai; Roberts, Susan; Gao, Min; Kadow, John [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3142 - 3147]

21
[ 220227-84-9 ]
[ 1311150-69-2 ]
[ 1311151-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In dichloromethane at 20℃;

Reference： [1]Location in patent: scheme or table Gentles, Robert G.; Ding, Min; Zheng, Xiaofan; Chupak, Louis; Poss, Michael A.; Beno, Brett R.; Pelosi, Lenore; Liu, Mengping; Lemm, Julie; Wang, Ying-Kai; Roberts, Susan; Gao, Min; Kadow, John [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3142 - 3147]

22
[ 220227-84-9 ]
[ 1181265-43-9 ]
[ 1349643-69-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With triethylamine In dichloromethane for 16h;	2,8-Diazaspiro[5.5]undecan-1 -one hydrogen chloride (107 mg, 0.524 mmol) was dissolved in dichloromethane (5 mL) and triethylamine (0.146 mL, 1.047 mmol). Then 3-[(trifluoromethyl)oxy]benzenesulfonyl chloride (0.098 mL, 0.577 mmol) was added and stirred for 16 h. The reaction mixture was concentrated in vacuo and the resulting residue was purified by MDAP to give 8-({3-[(trifluoromethyl)oxy]phenyl}- sulfonyl)-2,8-diazaspiro[5.5]undecan-1 -one (76 mg, 0.192 mmol, 37% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.46 - 1 .74 (m, 7 H) 1.83 - 1 .92 (m, 1 H) 2.15 - 2.26 (m, 1 H) 2.41 (d, J=1 1 .67 Hz, 1 H) 3.10 (br. s., 2 H) 3.47 (d, J=1 1 .67 Hz, 1 H) 3.68 (d, J=1 1 .07 Hz, 1 H) 7.53 (br. s., 1 H) 7.68 (br. s., 1 H) 7.74 - 7.84 (m, 3 H). MS ES+ve m/z 393 (M+H).

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC. - WO2011/141728, 2011, A1 Location in patent: Page/Page column 29-30

23
[ 220227-84-9 ]
[ 1187173-43-8 ]
[ 1349643-77-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With triethylamine; In dichloromethane; for 16.0h;	2,7-Diazaspiro[4.5]decan-1 -one hydrogen chloride (100 mg, 0.524 mmol) was dissolved in dichloromethane (5 mL) and triethylamine (0.146 mL, 1 .047 mmol). Then 3-[(trifluoromethyl)oxy]benzenesulfonyl chloride (0.098 mL, 0.577 mmol) was added and stirred for 16 h. The reaction mixture was concentrated in vacuo and the resulting residue was purified by MDAP to give 7-({3-[(trifluoromethyl)oxy]phenyl}- sulfonyl)-2,7-diazaspiro[4.5]decan-1 -one (85 mg, 0.222 mmol, 42% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1 .32 - 1 .48 (m, 2 H) 1.50 - 1 .64 (m, 1 H) 1 .65 - 1 .75 (m, 1 H) 1.89 - 1 .98 (m, 1 H) 1.99 - 2.09 (m, 1 H) 2.18 - 2.28 (m, 2 H) 3.19 (t, J=7.10 Hz, 2 H) 3.30 - 3.37 (m, 1 H) 3.65 (d, J=1 1 .62 Hz, 1 H) 7.69 (s, 1 H) 7.73 - 7.85 (m, 4 H). MS ES+ve m/z 379 (M+H).

Reference： [1]Patent: WO2011/141728,2011,A1 .Location in patent: Page/Page column 32-33

24
[ 220227-84-9 ]
[ 832710-65-3 ]
[ 1349632-98-9 ]

Yield	Reaction Conditions	Operation in experiment
49%	With triethylamine; In dichloromethane; for 16h;	2,8-Diazaspiro[4.5]decan-1 -one hydrogen chloride (100 mg, 0.524 mmol) was dissolved in dichloromethane (5 mL) and triethylamine (0.146 mL, 1.047 mmol). Then 3-[(trifluoromethyl)oxy]benzenesulfonyl chloride (0.098 mL, 0.577 mmol) was added and stirred for 16 h. The reaction mixture was concentrated in vacuo and the resulting residue was purified by MDAP to give 8-({3-[(trifluoromethyl)oxy]phenyl}- sulfonyl)-2,8-diazaspiro[4.5]decan-1 -one (99 mg, 0.259 mmol, 49% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1 .44 (ddd, J=13.41 , 3.55, 3.32 Hz, 2 H) 1 .60 - 1 .71 (m, 2 H) 1 .76 (t, J=6.80 Hz, 2 H) 2.57 - 2.69 (m, 2 H) 3.09 (t, J=6.82 Hz, 2 H) 3.45 - 3.54 (m, 2 H) 7.60 (s, 1 H) 7.68 (dd, J=1.67, 0.79 Hz, 1 H) 7.74 - 7.83 (m, 3 H). MS ES+ve m/z 379 (M+H)

Reference： [1]Patent: WO2011/141729,2011,A1 .Location in patent: Page/Page column 27-28

25
[ 220227-84-9 ]
[ 1187173-73-4 ]
[ 1349632-89-8 ]

Yield	Reaction Conditions	Operation in experiment
35%	With triethylamine In dichloromethane for 16h;	2,9-Diazaspiro[5.5]undecan-1 -one hydrogen chloride (107 mg, 0.524 mmol) was dissolved in dichloromethane (5 mL) and triethylamine (0.146 mL, 1 .047 mmol). Then 3-[(trifluoromethyl)oxy]benzenesulfonyl chloride (0.098 mL, 0.577 mmol) was added and stirred for 16 h. The reaction mixture was concentrated in vacuo and the resulting residue was purified by MDAP to give 9-({3-[(trifluoromethyl)oxy]phenyl}- sulfonyl)-2,9-diazaspiro[5.5]undecan-1 -one (73 mg, 0.184 mmol, 35% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.37 - 1 .54 (m, 4 H) 1.54 - 1 .64 (m, 2 H) 1.86 - 1.96 (m, 2 H) 2.86 (ddd, J=1 1 .91 , 8.78, 3.21 Hz, 2 H) 3.04 (td, J=5.82, 2.00 Hz, 2 H) 3.26 - 3.32 (m, 2 H) 7.30 (br. s., 1 H) 7.67 (s, 1 H) 7.72 - 7.85 (m, 3 H). MS ES+ve m/z 393 (M+H)

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC. - WO2011/141729, 2011, A1 Location in patent: Page/Page column 23-24

26
[ 220227-84-9 ]
[ 187235-71-8 ]
[ 1353753-72-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Blaser, Adrian; Palmer, Brian D.; Sutherland, Hamish S.; Kmentova, Iveta; Franzblau, Scott G.; Wan, Baojie; Wang, Yuehong; Ma, Zhenkun; Thompson, Andrew M.; Denny, William A. [Journal of Medicinal Chemistry, 2012, vol. 55, # 1, p. 312 - 326]

27
[ 220227-84-9 ]
[ 187235-71-8 ]
[ 1353753-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C

Reference： [1]Blaser, Adrian; Palmer, Brian D.; Sutherland, Hamish S.; Kmentova, Iveta; Franzblau, Scott G.; Wan, Baojie; Wang, Yuehong; Ma, Zhenkun; Thompson, Andrew M.; Denny, William A. [Journal of Medicinal Chemistry, 2012, vol. 55, # 1, p. 312 - 326]

28
[ 220227-84-9 ]
[ 20989-33-7 ]
[ 1360613-90-6 ]

Yield	Reaction Conditions	Operation in experiment
31%	With pyridine In dichloromethane at 0 - 20℃; for 16.5h;	4.2.5. General procedure for synthesis of sulfonamides of 17-amino-1,3,5(10)-estratrien-3-ol General procedure: To a stirred solution of 17-amino-1,3,5(10)-estratrien-3-ol (0.38 mmol) in dry pyridine (3 mL) at 0 °C was added a solution of the sulfonyl chlorides (0.40 mmol) in dichloromethane (1 mL) via a syringe pump over 30 min. After addition, the reaction was stirred for 16 h at room temperature. The pyridine was removed under vacuum, the residue was dissolved in ethyl acetate, washed with water and brine then dried (Na2SO4,), filtered, and concentrated and the residue purified by column chromatography.

Reference： [1]Location in patent: experimental part Mostafa, Yaser A.; Taylor, Scott D. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 4, p. 1535 - 1544]

29
[ 220227-84-9 ]
[ 91-21-4 ]
[ 1241617-98-0 ]

Yield	Reaction Conditions	Operation in experiment
3%	In acetone at 0 - 20℃; for 93h; Inert atmosphere;

Reference： [1]Jamieson, Stephen M. F.; Brooke, Darby G.; Heinrich, Daniel; Atwell, Graham J.; Silva, Shevan; Hamilton, Emma J.; Turnbull, Andrew P.; Rigoreau, Laurent J. M.; Trivier, Elisabeth; Soudy, Christelle; Samlal, Sharon S.; Owen, Paul J.; Schroeder, Ewald; Raynham, Tony; Flanagan, Jack U.; Denny, William A. [Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7746 - 7758]

30
[ 220227-84-9 ]
[ 1402141-64-3 ]
[ 1402141-54-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; aniline at 0 - 20℃; Inert atmosphere;

Reference： [1]Chen, Jianfang; Zhou, Haibin; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Yang, Chao-Yie; Wang, Shaomeng; Meagher, Jennifer L.; Stuckey, Jeanne A. [Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8502 - 8514,13]

31
[ 220227-84-9 ]
[ 1409937-61-6 ]
C₂₃H₂₄F₄N₂O₆S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; N-ethyl-N,N-diisopropylamine at 25 - 50℃; Inert atmosphere;

Reference： [1]Shao, Pengcheng P.; Ye, Feng; Chakravarty, Prasun K.; Varughese, Deepu J.; Herrington, James B.; Dai, Ge; Bugianesi, Randal M.; Haedo, Rodolfo J.; Swensen, Andrew M.; Warren, Vivien A.; Smith, McHardy M.; Garcia, Maria L.; McManus, Owen B.; Lyons, Kathryn A.; Li, Xiaohua; Green, Mitchell; Jochnowitz, Nina; McGowan, Erin; Mistry, Shruti; Sun, Shu-Yu; Abbadie, Catherine; Kaczorowski, Gregory J.; Duffy, Joseph L. [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9847 - 9855]

32
[ 220227-84-9 ]
[ 1416903-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; sodium sulfite / water / 0.5 h / 100 °C / Microwave irradiation 1.2: 0.33 h / 100 °C / Microwave irradiation 2.1: sodium ethanolate / ethanol / Reflux 3.1: trichlorophosphate; pyridine / 3 h / 110 °C 4.1: triethylamine / N,N-dimethyl-formamide / 3 h / 120 °C

Reference： [1]Kim, Junwon; Kwon, Jeongjin; Lee, Doohyun; Jo, Suyeon; Park, Dong-Sik; Choi, Jihyun; Park, Eunjung; Hwang, Jong Yeon; Ko, Yoonae; Choi, Inhee; Ju, Moon Kyeong; Ahn, Jiye; Kim, Junghwan; Han, Sung-Jun; Kim, Tae-Hee; Cechetto, Jonathan; Nam, Jiyoun; Ahn, Sujin; Sommer, Peter; Liuzzi, Michel; No, Zaesung; Lee, Jinhwa [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 153 - 157]

33
[ 220227-84-9 ]
[ 1416903-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; sodium sulfite / water / 0.5 h / 100 °C / Microwave irradiation 1.2: 0.33 h / 100 °C / Microwave irradiation 2.1: sodium ethanolate / ethanol / Reflux 3.1: trichlorophosphate; pyridine / 3 h / 110 °C

Reference： [1]Kim, Junwon; Kwon, Jeongjin; Lee, Doohyun; Jo, Suyeon; Park, Dong-Sik; Choi, Jihyun; Park, Eunjung; Hwang, Jong Yeon; Ko, Yoonae; Choi, Inhee; Ju, Moon Kyeong; Ahn, Jiye; Kim, Junghwan; Han, Sung-Jun; Kim, Tae-Hee; Cechetto, Jonathan; Nam, Jiyoun; Ahn, Sujin; Sommer, Peter; Liuzzi, Michel; No, Zaesung; Lee, Jinhwa [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 153 - 157]

34
[ 220227-84-9 ]
[ 1416903-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; sodium sulfite / water / 0.5 h / 100 °C / Microwave irradiation 1.2: 0.33 h / 100 °C / Microwave irradiation 2.1: sodium ethanolate / ethanol / Reflux

Reference： [1]Kim, Junwon; Kwon, Jeongjin; Lee, Doohyun; Jo, Suyeon; Park, Dong-Sik; Choi, Jihyun; Park, Eunjung; Hwang, Jong Yeon; Ko, Yoonae; Choi, Inhee; Ju, Moon Kyeong; Ahn, Jiye; Kim, Junghwan; Han, Sung-Jun; Kim, Tae-Hee; Cechetto, Jonathan; Nam, Jiyoun; Ahn, Sujin; Sommer, Peter; Liuzzi, Michel; No, Zaesung; Lee, Jinhwa [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 153 - 157]

35
[ 220227-84-9 ]
[ 107-14-2 ]
[ 797036-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-[(trifluoromethyl)oxy]benzenesulfonyl chloride With sodium hydrogencarbonate; sodium sulfite In water at 100℃; for 0.5h; Microwave irradiation; Stage #2: chloroacetonitrile In water at 100℃; for 0.333333h; Microwave irradiation;

Reference： [1]Kim, Junwon; Kwon, Jeongjin; Lee, Doohyun; Jo, Suyeon; Park, Dong-Sik; Choi, Jihyun; Park, Eunjung; Hwang, Jong Yeon; Ko, Yoonae; Choi, Inhee; Ju, Moon Kyeong; Ahn, Jiye; Kim, Junghwan; Han, Sung-Jun; Kim, Tae-Hee; Cechetto, Jonathan; Nam, Jiyoun; Ahn, Sujin; Sommer, Peter; Liuzzi, Michel; No, Zaesung; Lee, Jinhwa [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 153 - 157]

36
[ 220227-84-9 ]
[ 1423077-08-0 ]
[ 1423077-73-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 2h;	54 Example 54 - Synthesis of N-(3-(3-chloro-10,l l-dihydro-5H-dibenzo[b,f]azepin-5- yl)propyl)-3-(trifluoromethoxy)benzenesulfonamide. [00158] A solution of 3-(3-chloro-10,l l-dihydro-5H-dibenzo[£/]azepin-5-yl)propan- 1-amine hydrochloride (0.0700 g, 0.217 mmol) in DMF (1.0 mL) was cooled to 0 °C, treated with Et3N (63.0 μί, 0.455 mmol), and 3-trifluoromethoxybenzenesulfonyl chloride (0.58 mL, 3.40 mmol). The mixture was warmed to 25 °C, and stirred for 2 h. The mixture was partitioned between saturated aqueous NaCl (100 mL), and CH2CI2 (300 mL). The organic layer was washed with saturated aqueous NaCl (2 x 100 mL), dried (Na2S04), and concentrated in vacuo. The residue was dissolved in a minimal amount of CH2CI2 and purified by flash chromatography (S1O2, 0-20% ethyl acetate-hexanes) to afford the title compound as a clear film (0.104 g, 94%). 1H NMR (600 MHz, CDCI3) δ 7.67 (2H, br s), 7.46 (1H, t, J= 8.4 Hz), 7.39 (1H, d, J= 8.4 Hz), 7.12 (2H, m), 6.96 (3H, m), 6.96 (1H, m), 6.88 (1H, d, J= 7.2 Hz), 5.02 (1H, t, J = 5.4 Hz), 3.68 (2H, t, J= 6.0 Hz), 3.05 (4H, br s), 3.00 (2H, q, J= 6.6 Hz), 1.73 (2H, quintet, J= 6.6 Hz); 13C NMR (600 MHz, CDC13) δ 149.4, 148.8, 147.4, 142.1, 135.1, 131.8, 131.7, 131.5, 131.0, 129.8, 126.8, 125.3, 125.0, 123.8, 122.6, 121.3, 120.3, 119.8, 119.7, 47.3, 41.2, 32.0, 31.4, 27.5; LCMS m/z 511.0821 ([M C24H22CIF3N2O3S requires 511.1065).
94%	With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 2h;	RTC-26:N-(3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-3-(trifluoromethoxy)benzenesulfonamide A solution of 3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-amine hydrochloride (0.070 g, 0.217 mmol) in DMF (1.0 mL) was cooled to 0 C, treated with Et3N (63.0 µL, 0.455 mmol), and 3-trifluoromethoxybenzenesulfonyl chloride (0.58 mL, 3.40 mmol). The mixture was warmed to 25 C, and stirred for 2 h. The mixture was partitioned between saturated aqueous NaCl (100 mL), and CH2Cl2 (300 mL). The organic layer was washed with saturated aqueous NaCl (2 100 mL), dried (Na2SO4), and concentrated in vacuo. The residue was dissolved in a minimal amount of CH2Cl2 and purified by flash chromatography (SiO2, 0-20% ethyl acetate-hexanes) to afford the title compound as a clear film (0.104 g, 94%). 1H NMR (600 MHz, CDCl3) 7.67 (2H, br s), 7.46 (1H, t, J = 8.4 Hz), 7.39 (1H, d, J = 8.4 Hz), 7.12 (2H, m), 6.96 (3H, m), 6.96 (1H, m), 6.88 (1H, d, J = 7.2 Hz), 5.02 (1H, t, J = 5.4 Hz), 3.68 (2H, t, J = 6.0 Hz), 3.05 (4H, br s), 3.00 (2H, q, J = 6.6 Hz), 1.73 (2H, quintet, J = 6.6 Hz); 13C NMR (600 MHz, CDCl3) 149.4, 148.8, 147.4, 142.1, 135.1, 131.8, 131.7, 131.5, 131.0, 129.8, 126.8, 125.3, 125.0, 123.8, 122.6, 121.3, 120.3, 119.8, 119.7, 47.3, 41.2, 32.0, 31.4, 27.5; LCMS m/z 511.1 ([M + H+], C24H22ClF3N2O3S requires 511.1).

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI - WO2013/25882, 2013, A2 Location in patent: Paragraph 00158
[2]Kastrinsky, David B.; Sangodkar, Jaya; Zaware, Nilesh; Izadmehr, Sudeh; Dhawan, Neil S.; Narla, Goutham; Ohlmeyer, Michael [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6528 - 6534]

37
[ 220227-84-9 ]
[ 1428966-45-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With dmap; hydroxylamine hydrochloride In pyridine at 20℃; for 0.0833333h; Cooling with ice;	Synthesis of N-hydroxyarylsulfonamide derivatives. General procedure: To a mixture of hydroxylamine hydrochloride (2 equiv.) and DMAP (2 equiv.) in pyridine (20 mL) was added a portion of arylsulfonyl chloride (1 equiv.) on an ice-bath. Then, the mixture was stirred for 5 min at room temperature. The resulting suspension was poured into AcOEt (100 mL) and 1 N HCl aq. (100 mL). The AcOEt layer was separated, washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography under one of the gradient conditions indicated below, and recrystallized from Et2O/n-hexane to give N-hydroxyarylsulfonamide derivatives.

Reference： [1]Aizawa, Kazuyuki; Nakagawa, Hidehiko; Matsuo, Kazuya; Kawai, Kodai; Ieda, Naoya; Suzuki, Takayoshi; Miyata, Naoki [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2340 - 2343]

38
[ 220227-84-9 ]
[ 134-20-3 ]
[ 1016062-88-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In tetrahydrofuran at 20℃; for 9h;