[ CAS No. 1623-93-4 ] {[proInfo.proName]}

Name: 1623-93-4|Biphenyl-4-sulfonyl Chloride|95%
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SKU: A147186
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Quality Control of [ 1623-93-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1623-93-4 ]

CAS No. :	1623-93-4	MDL No. :	MFCD00078658
Formula :	C₁₂H₉ClO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ALBQXDHCMLLQMB-UHFFFAOYSA-N
M.W :	252.72	Pubchem ID :	74192
Synonyms :	p-Phenylbenzenesulfonyl chloride;Biphenyl-4-sulfonyl chloride;p-Biphenylsulfonyl chloride;4-Phenylbenzenesulfonyl chloride	Chemical Name :	Biphenyl-4-sulfonyl Chloride

Calculated chemistry of [ 1623-93-4 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	64.96
TPSA :	42.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.26
Log Po/w (XLOGP3) :	3.7
Log Po/w (WLOGP) :	4.36
Log Po/w (MLOGP) :	3.07
Log Po/w (SILICOS-IT) :	2.93
Consensus Log Po/w :	3.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.16
Solubility :	0.0174 mg/ml ; 0.000069 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.28
Solubility :	0.0132 mg/ml ; 0.000052 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.46
Solubility :	0.000876 mg/ml ; 0.00000347 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 1623-93-4 ]

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:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1623-93-4 ]

* 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 [ 1623-93-4 ]
Downstream synthetic route of [ 1623-93-4 ]

[ 1623-93-4 ] Synthesis Path-Upstream 1~4

1
[ 92-52-4 ]
[ 1623-93-4 ]

Reference： [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 78, # 1-4, p. 55 - 70
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 23, p. 7486 - 7494
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4291 - 4309
[4] Archiv der Pharmazie, 2017, vol. 350, # 1,

2
[ 2113-68-0 ]
[ 1623-93-4 ]

Reference： [1] Archiv der Pharmazie, 2017, vol. 350, # 1,
[2] Journal of Organic Chemistry, 1988, vol. 53, # 10, p. 2367 - 2371
[3] J. Appl. Chem. USSR (Engl. Transl.), 1980, vol. 53, # 7, p. 1264 - 1268[4] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1980, vol. 53, # 7, p. 1619 - 1623
[5] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 2971 - 2979
[6] Journal of Medicinal Chemistry, 2000, vol. 43, # 2, p. 156 - 166
[7] Patent: US2002/95041, 2002, A1,
[8] Patent: US5998470, 1999, A,
[9] Patent: US5464853, 1995, A,
[10] Patent: US5571821, 1996, A,
[11] Patent: US6342610, 2002, B2, . Location in patent: Page column 140
[12] Patent: US6335324, 2002, B1, . Location in patent: Page column 105

3
[ 92-67-1 ]
[ 1623-93-4 ]

Reference： [1] Tetrahedron, 2003, vol. 59, # 8, p. 1317 - 1325

4
[ 92-66-0 ]
[ 1623-93-4 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8274 - 8276

[ 1623-93-4 ] Synthesis Path-Downstream 1~65

1
[ 1234-35-1 ]
[ 1623-93-4 ]
[ 162611-59-8 ]

Reference： [1]Journal fur Praktische Chemie - Chemiker-Zeitung,1995,vol. 337,p. 12 - 17

2
[ 1623-93-4 ]
[ 6530-09-2 ]
Biphenyl-4-sulfonic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2971 - 2979

3
[ 1623-93-4 ]
[ 28607-46-7 ]
[ 193810-34-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 4-methyl-morpholine In dichloromethane for 2h; Ambient temperature;

Reference： [1]Tamura, Yoshinori; Watanabe, Fumihiko; Nakatani, Takuji; Yasui, Ken; Fuji, Masahiro; Komurasaki, Tadafumi; Tsuzuki, Hiroshige; Maekawa, Ryuji; Yoshioka, Takayuki; Kawada, Kenji; Sugita, Kenji; Ohtani, Mitsuaki [Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 640 - 649]

4
[ 1623-93-4 ]
[ 103733-65-9 ]
[ 191326-92-8 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 11512 - 11513
[2]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3529 - 3544

5
[ 1623-93-4 ]
[ 33084-49-0 ]
[ 166964-10-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 141

6
[ 1623-93-4 ]
[ 177948-33-3 ]
4-[(biphenyl-4-sulfonylamino)-methoxycarbonyl-methyl]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

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

Reference： [1]Pikul; Ohler; Ciszewski; Laufersweiler; Almstead; De; Natchus; Hsieh; Janusz; Peng; Branch; King; Taiwo; Mieling [Journal of Medicinal Chemistry, 2001, vol. 44, # 16, p. 2499 - 2502]

7
[ 1623-93-4 ]
[ 4490-81-7 ]
[ 704888-95-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2441 - 2450

8
[ 1623-93-4 ]
[ 135-70-6 ]

Yield	Reaction Conditions	Operation in experiment
63 % Chromat.	With 1,1,1,2,2,2-hexamethyldisilane In ethylbenzene at 140℃; for 3h;

Reference： [1]Kashiwabara, Taigo; Tanaka, Masato [Tetrahedron Letters, 2005, vol. 46, # 42, p. 7125 - 7128]

9
[ 5699-54-7 ]
[ 1623-93-4 ]
2-(biphenyl-4-sulfonylamino)-3-methyl-butyric acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 311 - 316

10
[ 875-74-1 ]
[ 1623-93-4 ]
[ 193808-16-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide In diethyl ether at 20℃; for 16h;

Reference： [1]Malkov, Andrei V.; Bourhani, Zainaba; Kocovsky, Pavel [Organic and Biomolecular Chemistry, 2005, vol. 3, # 17, p. 3194 - 3200]

11
[ 1623-93-4 ]
[ 696-61-7 ]
[ 613-33-2 ]
[ 28952-41-2 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3345 - 3348

12
[ 1623-93-4 ]
[ 71989-31-6 ]
[ 3173-56-6 ]
[ 188970-92-5 ]
3-(3-benzyl-ureido)-2-[1-(biphenyl-4-sulfonyl)-pyrrolidine-2-carbonyl]-amino}-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5457 - 5462

13
[ 1623-93-4 ]
[ 166964-09-6 ]
N-(4-chloro-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrogenchloride; sodium hydroxide In tetrahydrofuran; methanol; water	200.b (b) (b) N-(4-Chloro-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide Sodium hydride (188 mg, 4.4 mmol) was suspended in dry THF (1 ml) and cooled to 0° C. A solution of 5-amino-4-chloro-3-methylisoxazole (mg, mmol) in dry THF (1 ml) was added with stirring. Once the addition was complete, the reaction mixture was warmed to room temperature for 10 min. The solution was recooled to 0° C., and 4-biphenylsulfonyl chloride (0.283 ml, 2.2 mmol) was added. Stirring was continued at 25° C. for 2 h. Excess sodium hydride was decomposed by the addition of methanol (0.4 ml) followed by water (0.5 ml). The THF was removed under reduced pressure and the residue was dissolved in water (20 ml) and basified by addition of sodium hydroxide (pH 9-10). Neutral impurities were removed by extraction with ethyl acetate (210 ml). The aqueous layer was acidified to pH 2-3 using concentrated HCl and extracted with ethyl acetate (310 ml). The combined organic layer was dried over magnesium sulfate. Removal of the solvent gave N-(4-chloro-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide in 83% yield. This product was purified by recrystallization from ethyl acetate/hexanes as a white solid, m.p. 129-132° C.
83%	With sodium hydride In tetrahydrofuran at 0 - 25℃; for 2.16667h;
83%	With hydrogenchloride; sodium hydroxide In tetrahydrofuran; methanol; water	7.b (b) (b) N-(4-Chloro-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide Sodium hydride (188 mg, 4.4 mmol) was suspended in dry THF (1 ml) and cooled to 0° C. A solution of 5-amino-4-chloro-3-methylisoxazole (mg, mmol) in dry THF (1 ml) was added with stirring. Once the addition was complete, the reaction mixture was warmed to room temperature for 10 min. The solution was recooled to 0° C., and 4-biphenylsulfonyl chloride (0.283 ml, 2.2 mmol) was added. Stirring was continued at 25° C. for 2 h. Excess sodium hydride was decomposed by the addition of methanol (0.4 ml) followed by water (0.5 ml). THF was removed under reduced pressure and the residue was dissolved in water (20 ml) and basified by addition of sodium hydroxide (pH 9-10). Neutral impurities were removed by extraction with ethyl acetate (210 ml). The aqueous layer was acidified to pH 2-3 using concentrated HCl and extracted with ethyl acetate (310 ml). The combined organic layer was dried over magnesium sulfate. Removal of the solvent gave N-(4-chloro-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide in 83% yield. This product was purified by recrystallization from ethyl acetate/hexanes as a white solid, m.p. 129°-132° C.

83%

With hydrogenchloride; sodium hydroxide In tetrahydrofuran; methanol; water

95.b (b) (b) N-(4-Chloro-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide Sodium hydride (188 mg, 4.4 mmol) was suspended in dry THF (1 ml) and cooled to 0° C. A solution of 5-amino-4-chloro-3-methylisoxazole (mg, mmol) in dry THF (1 ml) was added with stirring. Once the addition was complete, the reaction mixture was warmed to room temperature for 10 min. The solution was recooled to 0° C., and 4-biphenylsulfonyl chloride (0.283 ml, 2.2 mmol) was added. Stirring was continued at 25° C. for 2 h. Excess sodium hydride was decomposed by the addition of methanol (0.4 ml) followed by water (0.5 ml). THF was removed under reduced pressure and the residue was dissolved in water (20 ml) and basified by addition of sodium hydroxide (pH 9-10). Neutral impurities were removed by extraction with ethyl acetate (2*10 ml). The aqueous layer was acidified to pH 2-3 using concentrated HCl and extracted with ethyl acetate (3*10 ml). The combined organic layer was dried over magnesium sulfate. Removal of the solvent gave N-(4-chloro-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide in 83% yield. This product was purified by recrystallization from ethyl acetate/hexanes as a white solid, m.p. 129°-132° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US2002/95041, 2002, A1
[2]Current Patent Assignee: PFIZER INC - US6342610, 2002, B2 Location in patent: Page column 143
[3]Current Patent Assignee: PFIZER INC - US5464853, 1995, A
[4]Current Patent Assignee: PFIZER INC - US5571821, 1996, A

14
[ 5819-40-9 ]
[ 1623-93-4 ]
N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%
5%		199.b (b) (b) N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide was prepared, using the method in Example 193b, from 3-amino-4-bromo-5-methylisoxazole and 4-biphenylsulfonyl chloride in 5% yield. The crude product was purified by column chromatography. After recrystallization from ethyl acetate/hexanes, N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide (m.p. 154-156° C.) was obtained in 51% yield.

Reference： [1]Current Patent Assignee: PFIZER INC - US6342610, 2002, B2 Location in patent: Page column 142
[2]Current Patent Assignee: PFIZER INC - US2002/95041, 2002, A1

15
[ 57493-24-0 ]
[ 1623-93-4 ]
[ 376349-14-3 ]

Yield	Reaction Conditions	Operation in experiment
		17.A N-[4-(3-nitrophenyl)-1,3-thiazol-2-yl][1,1'-biphenyl]-4-sulfonamide 263A N-[4-(3-nitrophenyl)-1,3-thiazol-2-yl][1,1'-biphenyl]-4-sulfonamide The title compound was prepared from 2-amino-4-(-3-nitrophenyl)thiazole and 4-phenylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a yellow solid (25.8 mg) with purity >80%. MS (pos) m/z 438.1.

Reference： [1]Current Patent Assignee: CLARIO TECH LIMITED - US2003/166689, 2003, A1

16
[ 1623-93-4 ]
[ 21344-90-1 ]
[ 376349-50-7 ]

Yield	Reaction Conditions	Operation in experiment
		295A N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl][1,1'-biphenyl]-4-sulfonamide The title compound was prepared from <strong>[21344-90-1]4-(2-chlorophenyl)-1,3-thiazol-2-amine</strong> and 4-phenylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a white solid (31.8 mg) with purity >90percent. MS (pos) m/z 427.1.

Reference： [1]Patent: US2003/166689,2003,A1

17
[ 1623-93-4 ]
[ 30235-27-9 ]
[ 376349-46-1 ]

Yield	Reaction Conditions	Operation in experiment
		291A N-[4-(3-pyridinyl)-1,3-thiazol-2-yl][1,1'-biphenyl]-4-sulfonamide The tide compound was prepared from 4-(3-pyridyl)-1,3-thiazol-2-amine and 4-phenylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a white-yellow solid (1.4 mg) with purity >80%. MS (pos) m/z 394.2.

Reference： [1]Patent: US2003/166689,2003,A1

18
[ 5683-33-0 ]
[ 1623-93-4 ]
[ 33084-49-0 ]
N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenyisulfonamide [ No CAS ]
[ 166964-10-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	In pyridine;	(b) N-(4-Biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-dimethyl-aminopyridine (5 mg) was added, and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1 N HCl (2*50 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography using 8:2, hexanes/ethyl acetate, to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenyisulfonamide.

Reference： [1]Patent: US2002/95041,2002,A1

19
[ 1623-93-4 ]
[ 7440-44-0 ]
[ 103733-65-9 ]
[ 191326-92-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium hydroxide; In tetrahydrofuran; water;	Reference Example 3 Sodium hydroxide (13.6 g) is dissolved in water (300 ml), and therein is suspended <strong>[103733-65-9](3R)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid</strong> (30.0 g) and thereto is added tetrahydrofuran (120 ml). To the resulting solution is added 4-biphenylylsulfonyl chloride (42.9 g), and the mixture is stirred at room temperature for one hour. The reaction mixture is acidified with 10% hydrochloric acid under ice cooling, and is diluted with water, and then extracted twice with ethyl acetate. The extract is washed with water and an aqueous saturated saline solution, dried over sodium sulfate and then treated with active carbon. Undissolved materials are filtered off from the extract, and the solvent is distilled off under reduced pressure. The residue is recrystallized from ethyl acetate-hexane to give (3R)-N-(4-biphenylylsulfonyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (36.5 g) as colorless crystals. Yield: 55% m.p.: 195-202 C. [alpha] D29: +8.02 (c=1.08, dimethylformamide) IR (Nujol, cm-1): 3300, 2924, 1743, 1456 MS (m/z): 394 (MH+); NMR (300 MHz, CDCI3, delta): 3.10-3.15 (2H, m), 4.48 (1H, d, J=15.6 Hz), 4.67 (1H, d, J=15.6 Hz), 4.93 (1H, dd, J=4.0 and 5.3 Hz), 6.95-7.20 (4H, m), 7.40-7.53 (3H, m), 7.56-7.69 (4H, m), 7.83-7.88 (2H, m)

Reference： [1]Patent: US5932732,1999,A

20
[ 5819-40-9 ]
[ 1623-93-4 ]
N-(4-Biphenylsulfonyl)-N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		94.b (b) (b) N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide ws prepared, using the method in Example 89b, from 3-amino-4-bromo-5-methylisoxazole and 4-biphenylsulfonyl chloride in 5% yield. The product (m.p. 154°-156° C.) was isolated in 51% yield by column chromatography, after recrystallization from ethyl acetate/hexanes. N-(4-Biphenylsulfonyl)-N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide was obtained in 51% yield.

Reference： [1]Current Patent Assignee: PFIZER INC - US5571821, 1996, A

21
[ 496-15-1 ]
[ 1623-93-4 ]
[ 25830-77-7 ]
2-(Biphenyl-4-sulfonylamino)-5-(2,3-dihydroindol-1-yl)-5-oxopentanecarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-indoline; N-phthaloyl-L-glutamic anhydride In 1,3-dioxane at 40℃; for 5h; Stage #2: With hydrazine In ethanol at 80℃; for 3h; Stage #3: 4-diphenylsulfonyl chloride With potassium carbonate In tetrahydrofuran; water at 20℃; for 6 - 8h;

Reference： [1]Current Patent Assignee: SANOFI - US6335333, 2002, B1 Location in patent: Page column 12

22
[ 70125-16-5 ]
[ 1623-93-4 ]
[ 1146771-40-5 ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 1378 - 1388

23
[ 1623-93-4 ]
[ 38385-95-4 ]
[ 1159096-81-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 18h;	To a stirred mixture of 4-biphenylsulfonyl chloride (63 mg, 0.25 mmol) and 2- (piperidin-4-yl)-lH-benzimidazole (50 mg, 0.25 mmol) in DCM (10 mL) is added N,N- diisopropylethylamine (62 muL, 0.37 mmol). After 18 h the reaction mixture is washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Trituration with heptane gives 21 mg of 2-[l-(biphenyl-4-ylsulfonyl)piperidin- 4-yl]-lH-benzimidazole

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2206 - 2210
[2]Patent: WO2010/80357,2010,A1 .Location in patent: Page/Page column 52

24
[ 640-68-6 ]
[ 1623-93-4 ]
(R)-2-(biphenyl-4-ylsulfonamido)-3-methylbutanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.2%	With triethylamine In 1,4-dioxane; water at 20℃; for 20h;	18 To a solution of D-valine (5.0 g, 42.68 mmol) and TEA (8.92 ml, 64.02 mmol) in H2O/diossano 1:1 (66.7 ml) was added biphenyl-4-sulfonyl chloride (11.86g, 46.95 mmol). After stirring at r.t. for 20 h, the mixture was diluted with CH2Cl2, washed with HCl 1N and the organic phase was dried and evaporated in vacuo. After recrystallization from n-hexane, the desired carboxylic acid (16) was obtained as a white solid (7.72 g, 54.2 % yield). 1H-NMR (CDCl3) δ: 0.83 (d, J= 6.7 Hz, 3H); 0.95 (d, J= 6.7 Hz, 3H); 2.00-2.16 (m, 1H); 2.46 (br s, 1H); 3.76-3.83 (dd, J= 4.4 Hz, J= 9.8 Hz, 1H); 5.15 (d, J= 9.8 Hz, 1H); 7.42-7.70 (m, 7H); 7.84-7.88 (m, 2H).
45%	With triethylamine In 1,4-dioxane; water at 20℃; for 18h;
40%	With triethylamine In 1,4-dioxane; water at 20℃; for 12h;

With triethylamine In 1,4-dioxane; water at 20℃;

Reference： [1]Current Patent Assignee: BRACCO SPA - EP2149568, 2010, A1 Location in patent: Page/Page column 32; 47
[2]Nuti, Elisa; Cuffaro, Doretta; D'Andrea, Felicia; Rosalia, Lea; Tepshi, Livia; Fabbi, Marina; Carbotti, Grazia; Ferrini, Silvano; Santamaria, Salvatore; Camodeca, Caterina; Ciccone, Lidia; Orlandini, Elisabetta; Nencetti, Susanna; Stura, Enrico A.; Dive, Vincent; Rossello, Armando [ChemMedChem, 2016, p. 1626 - 1637]
[3]Marques, Sérgio M.; Nuti, Elisa; Rossello, Armando; Supuran, Claudiu T.; Tuccinardi, Tiziano; Martinelli, Adriano; Santos, M. Amélia [Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 7968 - 7979]
[4]Location in patent: experimental part Marques, Sérgio M.; Tuccinardi, Tiziano; Nuti, Elisa; Santamaria, Salvatore; André, Vânia; Rossello, Armando; Martinelli, Adriano; Santos, M. Amélia [Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8289 - 8298]

25
[ 70125-16-5 ]
[ 1623-93-4 ]
[ 1262632-92-7 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 591 - 602

26
[ 70125-16-5 ]
[ 1623-93-4 ]
[ 1262632-87-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 591 - 602

27
[ 18472-06-5 ]
[ 1623-93-4 ]
[ 1262633-18-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 591 - 602

28
[ 14068-53-2 ]
[ 1623-93-4 ]
[ 1296884-91-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With pyridine at 20℃; for 4h;	N-(5-Ethyl-1,3,4-thiadiazol-2-yl)biphenyl-4-sulfonamide (42). General procedure: To a solution of p-phenylbenzenesulfonyl chloride (250 mg, 0.99 mmol) in pyridine (5 mL) was added 2-amino-1,3,4-thiadiazole (100 mg, 0.99 mmol) at rt. The reaction mixture was stirred for 4 h, then 2 M HCl (20 mL) was added to quench the reaction. The mixture was extracted with EtOAc (3×30 mL), the organic layer was washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:MeOH 19:1 to give the product 41 (178 mg, 0.56 mmol, 57% yield),

Reference： [1]Ahad, Ali Md.; Zuohe, Song; Du-Cuny, Lei; Moses, Sylvestor A.; Zhou, Li Li; Zhang, Shuxing; Powis, Garth; Meuillet, Emmanuelle J.; Mash, Eugene A. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 6, p. 2046 - 2054]

29
[ 1623-93-4 ]
[ 56951-58-7 ]
[ 1296884-92-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	With pyridine; at 20℃; for 4h;	General procedure: To a solution of p-phenylbenzenesulfonyl chloride (250 mg, 0.99 mmol) in pyridine (5 mL) was added 2-amino-1,3,4-thiadiazole (100 mg, 0.99 mmol) at rt. The reaction mixture was stirred for 4 h, then 2 M HCl (20 mL) was added to quench the reaction. The mixture was extracted with EtOAc (3×30 mL), the organic layer was washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:MeOH 19:1 to give the product 41 (178 mg, 0.56 mmol, 57% yield),

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2046 - 2054

30
[ 1623-93-4 ]
[ 152460-10-1 ]
[ 1349893-81-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h;	5.1.8. Synthesis of 4-chloro-N-(4-methyl-3-(4-(pyridin-4-yl)pyrimidin-2-ylamino)phenyl)benzene sulfonamide (3a) General procedure: To a stirred solution of compound 9a (277 mg, 1 mmol) in DMF, triethylamine (5.0 equiv) and catalytic amount of DMAP were added and cooled to 0-5 °C, then sulfonylchloride 10a (1 mmol) was added drop wise. The reaction mixture was stirred for 4-5 h at room temperature (completion of reaction was confirmed by TLC) then the reaction mixture was washed with water, followed by saturated NaCl solution. The aqueous layer extracted with ethyl acetate and dried over anhydrous sodium sulfate, evaporated in vacuum to afford the compound as yellow solid (360 mg, 80%).

Reference： [1]Location in patent: experimental part Kamal, Ahmed; Dastagiri; Janaki Ramaiah; Surendranadha Reddy; Vijaya Bharathi; Kashi Reddy; Victor Prem Sagar; Lakshminarayan Reddy; Pushpavalli; Pal-Bhadra, Manika [European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 5817 - 5824]

31
[ 30433-91-1 ]
[ 1623-93-4 ]
N-[2-(2-thienyl)ethyl]-(1,1'-biphenyl)-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine In dichloromethane at 0 - 20℃;	4.1.1. General procedure for the preparation of sulfonamides 8a-g, i-l, 9a-h and 10a-h, j General procedure: A solution of appropriate sulfonyl chloride 7a-l (10 mmol) in dichloromethane (15 mL) was slowly added to a cooled (0 °C) solution of amine 4-6 (15 mmol) in dichloromethane (10 mL) and triethylamine (15 mmol). The resulting mixture was stirred at room temperature overnight. The solvent was removed at reduced pressure, then the resulting residue was taken up in ethyl acetate and washed with a solution of HCl (1 M, 2 × 25 mL) and brine (2 × 25 mL). The organic phase was dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The title compounds were purified by crystallization from ethyl acetate/petroleum ether 40-60 °C. A similar procedure has been employed for the synthesis of 9f-h, 10f-g, while a different synthetic approach has been described for 10a-e, 10h-k; in all cases our 1H NMR spectral data matched those previously reported for these compounds [19b], [19c], [19d], [19e], [19f], [19g], [19h], [19i], [19] and [19a].

Reference： [1]Location in patent: experimental part Ramunno, Anna; Cosconati, Sandro; Sartini, Stefania; Maglio, Vita; Angiuoli, Sara; La Pietra, Valeria; Di Maro, Salvatore; Giustiniano, Mariateresa; La Motta, Concettina; Da Settimo, Federico; Marinelli, Luciana; Novellino, Ettore [European Journal of Medicinal Chemistry, 2012, vol. 51, p. 216 - 226]

32
[ 1623-93-4 ]
[ 259537-92-3 ]
C₁₇H₂₀N₂O₂S*C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7061 - 7079

33
[ 1623-93-4 ]
[ 259537-92-3 ]
C₂₂H₂₈N₂O₄S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7061 - 7079

34
[ 1623-93-4 ]
[ 53386-64-4 ]
[ 1456601-68-5 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 932 - 941

35
[ 4488-22-6 ]
[ 1623-93-4 ]
C₄₃H₃₂N₂O₂S [ No CAS ]
C₃₂H₂₄N₂O₂S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3684 - 3687
Angew. Chem.,2014,vol. 126,p. 3758 - 3761,4

36
[ 4488-22-6 ]
[ 1623-93-4 ]
[ 1613472-73-3 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3684 - 3687
Angew. Chem.,2014,vol. 126,p. 3758 - 3761,4

37
[ 1623-93-4 ]
[ 37663-44-8 ]
C₂₄H₂₃NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With pyridine; at 80℃;	The compound 3H-spiro [isobenzofuran- 1 ,4?-piperidine] hydrochloride (10mg, 0.O44mmol) and sulfonyl chloride (12mg, 0.O47mmol) were combined in pyridine (0.5m1) and stirred at 80 °C overnight, The solvent was removed and the residue was purified by preparative TLC to afford 14 mg of compound V:148 (mle=406[M+H]j, Yield: 78percent.

Reference： [1]Patent: WO2014/127350,2014,A1 .Location in patent: Page/Page column 157; 158

38
[ 1623-93-4 ]
[ 1446-61-3 ]
C₃₂H₃₉NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine; In dichloromethane; at 0 - 23℃;	To a solution of<strong>[1446-61-3](+)-dehydroabietylamine</strong> (1.0 mmol) and triethylamine (3.0 mmol) in CH2Cl2 (5 mL), a solution of the corresponding sulfonyl chloride (1.10 mmol) in CH2Cl2 (5 mL) at 0 C was slowly added dropwise via syringe. The resulting reaction mixture was allowed to be warmed up and stirred at 23 C for 1-12 hr based on reaction progress (TLC, MS) before it was quenched with an aqueous NH4Cl solution (10 mL). The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (5 mL x 3).The combined organic phase was dried over MgSO4 and concentrated under reduced pressure. The resulting crude product was purified via flash column chromatography (SiO2; isocratic eluent: 20% EtOAc in petroleum ether) to provide the sulfonamide product.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 9 - 13

39
[ 1623-93-4 ]
[ 107-95-9 ]
3-(biphenyl-4-sulfonylamino)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In 1,4-dioxane; water at 20℃;	4 5.1.4 3-(Biphenyl-4-ylsulfonamido)propanoic acid (4) Biphenyl-4-sulfonyl chloride (1.56 g, 6.17 mmol) was added to a solution of 3-aminopropanoic acid (500 mg, 5.61 mmol) in H2O (3.3 mL) and dioxane (3.3 mL) containing Et3N (1.17 mL, 8.4 mmol). The mixture was stirred at room temperature overnight, the dioxane was evaporated and the residue was treated with EtOAc and washed with HCl 1N and brine. Organic layers were then collected, dried over Na2SO4, and evaporated in vacuo. The crude product was triturated with n-hexane to yield carboxylate 4 as a white solid (1.16 g, 70% yield). Mp: 138-140 °C; 1H NMR [(CD3)2co] δ: 2.57 (t, J = 6.7 Hz, 2H); 3.18-3.27 (m, 2H); 6.60 (t, J = 5.4 Hz, 1H); 7.44-7.57 (m, 3H); 7.68-7.78 (m, 2H); 7.87-8.00 (m, 4H).
45%	With sodium hydroxide In water at 35℃; for 1h;	S.3 General method for the preparation of 3-arylsulfonylamino propionic acids 10 General procedure: To partially dissolved β-alanine (9) (0.6 g, 6.8 mmol) in distilled water (4 mL) was added a solution ofaqueous NaOH 2M (3.4 mL), followed by the portionwise addition of the different arylsulfonyl chloride2a-h, l (9.6 mmol). The reaction mixture was stirred at 35 °C and a solution of 1 M aqueous NaOH wasadded portionwise to maintain a pH of approximately 9. After complete consumption of alkali, stirringwas continued at 35 °C for an additional 1 h. Unreacted arylsulfonyl chloride was removed by filtration,and the reaction mixture was acidified with 5M aqueous HCl at 0 °C to pH 2. The aqueous solution withsolid precipitate was stored at 4 °C o.n. The crystals formed were collected by filtration, washed withcold water and dried at reduced pressure.

Reference： [1]Sjøli, Stian; Nuti, Elisa; Camodeca, Caterina; Bilto, Irina; Rossello, Armando; Winberg, Jan-Olof; Sylte, Ingebrigt; Adekoya, Olayiwola A. [European Journal of Medicinal Chemistry, 2016, vol. 108, p. 141 - 153]
[2]Bassetto, Marcella; Leyssen, Pieter; Neyts, Johan; Yerukhimovich, Mark M.; Frick, David N.; Courtney-Smith, Matthew; Brancale, Andrea [European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1115 - 1131]

40
[ 599183-36-5 ]
[ 1623-93-4 ]
N-(3-iodo-1H-indazol-5-yl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With pyridine In dichloromethane at 0℃; Inert atmosphere;	5.5 General procedure for the syntheses of compounds 12a-j General procedure: Method (i): To a solution of compound 11 [24] (600mg, 2.31mmol) in CH2Cl2 (11.55ml) was added pyridine (0.93ml, 11.55mmol). Phenyl isocyanate (0.51ml, 4.62mmol) was then added to the mixture under ice-bath, and stirred for 10min to complete the reaction. The reaction was quenched by adding water. The solvent was removed by vacuum. The resulting mixture was extracted by ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was then purified by silica gel column chromatography using the appropriate mobile phase to give the title compounds 12a. Method (ii): To a solution of compound 11 (300mg, 1.16mmol) in pyridine (0.47ml) was added benzoyl chloride (0.16ml, 1.39mmol) under ice-bath. The mixture was stirred for 10min, and then added with ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under vacuum. The residue was then purified by silica gel column chromatography using the appropriate mobile phase to give the title compounds 12b. Method (iii): A mixture of compound 11 (500mg, 1.93mmol) and benzaldehyde (0.39ml, 3.86mmol) in ethanol (9.65ml) was stirred for 10min. Catalytic amount of acetic acid was ejected to the mixture under ice-bath. A portion of NaBH4 (146mg, 3.86mmol) was slow added to the reaction. After stirred for 4h, water was added to quench the reaction. The solution was then removed by vacuum. The resulting mixture was extracted by ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was then purified by silica gel column chromatography using the appropriate mobile phase to give the title compounds 12c. Method (iv): To a stirred solution of compound 11 (500mg, 1.93mmol) and pyridine (0.78ml, 2.90mmol) in CH2Cl2 (9.65ml) was added dropwise benzenesulfonyl chloride under ice-bath for 10min. The mixture was quenched with water, and concentrated under vacuum. The resulting mixture was extracted by ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was then purified by silica gel column chromatography using the appropriate mobile phase to give the title compounds 12d-j.

Reference： [1]Chang, Chun-Feng; Lin, Wen-Hsing; Ke, Yi-Yu; Lin, Yih-Shyan; Wang, Wen-Chieh; Chen, Chun-Hwa; Kuo, Po-Chu; Hsu, John T.A.; Uang, Biing-Jiun; Hsieh, Hsing-Pang [European Journal of Medicinal Chemistry, 2016, vol. 124, p. 186 - 199]

41
[ 1623-93-4 ]
[ 145901-11-7 ]
N-(1H-pyrrolo[2,3-b]pyridin-6-yl)[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.6%	With pyridine; at 20℃; for 2h;	Pyridine (10 ml) to <strong>[145901-11-7]1H-pyrrolo[2,3-b]pyridin-6-amine</strong>(266 mg, 2 mmol) in a mixed solution was added [1,1'-biphenyl]-4-sulfonyl chloride It was added (500 mg, 2 mmol) and stirred for 2 hours at room temperature. The reaction mixture was concentrated and the residue was purified by graph silica gel (ethyl acetate: petroleum ether = 1: 2) to afford the title compound as a white solid (500 mg, 71.6% yield).

Reference： [1]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0115; 0116; 0119-0120

42
[ 1623-93-4 ]
[ 17609-80-2 ]
[ 1365658-22-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In tetrahydrofuran; at 20℃; for 12h;	General procedure: A mixture of sulfonyl chloride (1, 1 equiv), secondary amine (2, 1.5 equiv) and triethylamine (Et3N, 3 equiv) in anhydrous tetrahydrofuran (THF, 0.2 M) was stirred for 12 h at room temperature. Next, the reaction mixture was diluted and filtered with ethyl acetate (EtOAc). The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on SiO2 (Hexane: EtOAc: Methylene chloride = 3: 2: 1) to yield sulfonamide analogues (3-25).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5098 - 5102

43
[ 1623-93-4 ]
[ 4393-09-3 ]
N-(2,3-dihydroxyphenyl)methyl-4-diphenylsulfonamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 25 - 37

44
[ 1623-93-4 ]
[ 4393-09-3 ]
N-(2,3-dimethoxyphenyl)methyl-4-diphenylsulfonamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 25 - 37

45
[ 68-35-9 ]
[ 1623-93-4 ]
N-(4-(N-(pyrimidin-2-yl)sulfamoyl)phenyl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridine; In chloroform; for 48h;Reflux;	General procedure: New and modern synthetic protocols were used for the synthesis of sulfonamide derivatives [49]. Sulfonyl chloride (0.5 g, 1.85 mmol) in chloroform (10 mL) was added dropwise to a solution ofciprofloxacin/amantadine/<strong>[68-35-9]sulfadiazine</strong> or thiosemicarbazide (0.28 g, 1.85 mmol not valid for all these substrates) and pyridine (0.77 mL) in chloroform (5 mL) and stirred for 48 h. The reaction mixture was washed successively with 10% citric acid (5-10 mL), 10% NaHCO3 (5-10 mL) and water(3-10 mL), dried with MgSO4 and concentrated in vacuo. Purification by flash column chromatography(30% hexane-ethyl acetate) yielded the crude compound as a yellow oil. The oil was further purifiedby recrystallization from chloroform and a few drops of n-hexane. The characterization data for the compounds is given below.

Reference： [1]Molecules,2017,vol. 22

46
[ 1623-93-4 ]
[ 85721-33-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridine In chloroform at 20℃; for 48h;	4.2. Synthetic Procedures General procedure: New and modern synthetic protocols were used for the synthesis of sulfonamide derivatives [49]. Sulfonyl chloride (0.5 g, 1.85 mmol) in chloroform (10 mL) was added dropwise to a solution ofciprofloxacin/amantadine/sulfadiazine or thiosemicarbazide (0.28 g, 1.85 mmol not valid for all these substrates) and pyridine (0.77 mL) in chloroform (5 mL) and stirred for 48 h. The reaction mixture was washed successively with 10% citric acid (5-10 mL), 10% NaHCO3 (5-10 mL) and water(3-10 mL), dried with MgSO4 and concentrated in vacuo. Purification by flash column chromatography(30% hexane-ethyl acetate) yielded the crude compound as a yellow oil. The oil was further purifiedby recrystallization from chloroform and a few drops of n-hexane. The characterization data for the compounds is given below.

Reference： [1]Channar, Pervaiz Ali; Saeed, Aamer; Albericio, Fernando; Larik, Fayaz Ali; Abbas, Qamar; Hassan, Mubashir; Raza, Hussain; Seo, Sung-Yum [Molecules, 2017, vol. 22, # 8]

47
[ 1623-93-4 ]
[ 204255-11-8 ]
(3R,4R,5S)-5-(([1,1'-biphenyl]-4-sulfonamide))-4-acetamido-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In dichloromethane; at 20℃; for 6h;	General procedure: To a solution of <strong>[204255-11-8]oseltamivir phosphate</strong> (0.82 g, 2.0 mmol), 10 mLof triethylamine and 30 mL of acetonitrile or dichloromethane,arylsulfonyl chloridewas added (1.2 equiv.) The mixturewas stirredat room temperature for 6 h. After confirming the completion of thereaction by TLC, the solvent was evaporated under reduced pressure.Sodium chloride solution (30 mL) was added to the residueand extracted with ethyl acetate (3 40 mL). The combined organiclayer was washed twice with saturated sodium chloride (30 mL).And dried with anhydrous MgSO4, Then, filtered and the solventwas removed, the crude product was obtained, and purified bycolumn chromatography to obtain the corresponding intermediates16a-16g.
84.7%	With triethylamine; In dichloromethane; at 25 - 30℃; for 8h;	Weigh ostivastine phosphate (0.41 g, 1 mmol)[1,1'-biphenyl] -4-sulfonyl chloride (0.25 g, 1 mmol)In 20 mL of dichloromethane and5 mL of triethylamine solution,25-30 C for 8 h(TLC detection reaction finished developing agent: ethyl acetate). The solvent was evaporated, 30 mL of water was added, extracted three times with 30 mL of ethyl acetate, dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated and subjected to flash column chromatography to give a white solid which was compound (3R, 4R, 5S) -5- (Pentane-3-yloxy) cyclohexene-1-ene-1-carboxylate (12) ),Yield: 84.7%.

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 191
[2]Patent: CN107056636,2017,A .Location in patent: Paragraph 0238; 0239; 0240; 0241

48
[ 1623-93-4 ]
[ 25602-68-0 ]
8-(biphenyl-4-ylsulfonyl)-8-azabicyclo[3.2.1]octan-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With dmap; triethylamine; In dichloromethane; for 24h;	A 50 mL round bottom flask was charged with <strong>[25602-68-0]nortropinone hydrochloride</strong> (0.808 g, 5.00 mmol, 1.00 equiv.), dichloromethane (25 mL, c = 0.2 M), 4-biphenyl sulfonyl chloride (1.27 g, 5.00 mmol, 1.00 equiv.), triethylamine (2.0 g, 2.8 mL, 20 mmol, 4.0 equiv.) and 4- dimethylamino pyridine (61 mg, 0.50 mmol, 0.10 equiv.) were added. After 24 h the reaction mixture was diluted with dichloromethane (100 mL) and washed with 0.5 M HCI (150 mL). The aqueous layer was extracted with dichloromethane (3 chi 50 mL) and the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane and ethyl acetate (90: 10 (v/v)) to afford nortropinone (4- biphenyl))sulfonamide 2q (1.12 g, 3.27 mmol, 65percent) as a colorless solid. R = 0.40 (ethyl acetate/dichloromethane, 10:90 (v/v)). (0337) [00179] NMR Spectroscopy: 1H NMR (500 MHz, CDC13, 23 °C, delta): 7.97 (d, J= 8.8 Hz, 2H), 7.74 (d, J= 8.8 Hz, 2H), 7.63 - 7.59 (m, 2H), 7.52 - 7.46 (m, 2H), 7.45 - 7.41 (m, 1H), 4.55 (tt, J= 3.9, 2.1 Hz, 2H), 2.83 (dd, J = 16.4, 4.6 Hz, 2H), 2.48 - 2.27 (m, 2H), 1.84 - 1.74 (m, 2H), 1.66 - 1.59 (m, 2H) ppm. 13C NMR (126 MHz, CDC13, 23°C, delta): delta 206.9, 146.2, 139.1, 138.4, 129.2, 128.8, 127.9 (d, J= 1.6 Hz), 127.4, 56.2, 50.4, 29.5 ppm. HRMS-ESI (m/z) calculated for Ci9Hi9SiN03Na [M+Na]+, 364.0978; found, 364.0981

Reference： [1]Patent: WO2017/156265,2017,A1 .Location in patent: Paragraph 00178; 00179

49
[ 67455-41-8 ]
[ 1623-93-4 ]
C₃₄H₃₁N₃O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.6%	With triethylamine; In dichloromethane;	The product 22B was dissolved in dichloromethane (20 mL) and triethylamine (348 muL, 2.5 mM) and 4-biphenylsulfonyl chloride (455 mg, 1.8 mM) were added and stirred overnight.The reaction was monitored by TLC and concentrated. Column chromatography (dichloromethane/methanol=200/1) gave compound 22 (215 mg, yield 19.6%).

Reference： [1]Patent: CN107540636,2018,A .Location in patent: Paragraph 0235; 0237

50
[ 1623-93-4 ]
[ 94-32-6 ]
ethyl 4-{N-butyl[1,1’-biphenyl]-4-sulfonamido}benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With pyridine; dmap In dichloromethane at 40℃; for 18h; Inert atmosphere;	General procedure C: Sulfonamide formation; Synthesis of tertiary sulfonamides(compounds 2b-16b, 18b-35b, 36, 37b-39b and 41b-47b) General procedure: The secondary amine (E1, 1.0 eq) and dry pyridine (E2, 1.0 eq) were dissolved in 20 ml drydichloromethane. The benzenesulfonylchloride (E3, 1.0 eq) and a catalytically amount of 4-DMAP were added to the mixture. The reaction was stirred under argon-atmosphere andrefluxed for 18 h. The solvent was evaporated under reduced pressure, and the residue wassuspended in water. The product was extracted three times with ethyl acetate and the organiclayer was dried over MgSO4. Subsequently the solvent was evaporated again.Recrystallization or column chromatography gave the pure product.

Reference： [1]Cheung, Sun-Yee; Werner, Markus; Esposito, Lucia; Troisi, Fabiana; Cantone, Vincenza; Liening, Stefanie; König, Stefanie; Gerstmeier, Jana; Koeberle, Andreas; Bilancia, Rossella; Rizza, Roberta; Rossi, Antonietta; Roviezzo, Fiorentina; Temml, Veronika; Schuster, Daniela; Stuppner, Hermann; Schubert-Zsilavecz, Manfred; Werz, Oliver; Hanke, Thomas; Pace, Simona [European Journal of Medicinal Chemistry, 2018, vol. 156, p. 815 - 830]

51
[ 29897-82-3 ]
[ 1623-93-4 ]
3-([1,1'-biphenyl]-4-ylsulfonyl)-1-benzyl-1H-pyrrole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14787 - 14791
Angew. Chem.,2018,vol. 130,p. 15003 - 15007,5

52
[ 5819-40-9 ]
[ 1623-93-4 ]
N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%		6.b (b) (b) N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide N-(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide was prepared, using the method in Example 1 b, from 3-amino-4-bromo-5-methylisoxazole and 4-biphenylsulfonyl chloride in 5% yield. The product (m.p. 154°-156° C.) was isolated in 51% yield by column chromatography, after recrystallization from ethyl acetate/hexanes. N-(4-Biphenylsulfonyl)-No(4-bromo-5-methyl-3-isoxazolyl)-4-biphenylsulfonamide was obtained in 51% yield.

Reference： [1]Current Patent Assignee: PFIZER INC - US5464853, 1995, A

53
[ 1623-93-4 ]
[ 33084-49-0 ]
[ 166964-10-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dmap; In pyridine; ethyl acetate;	(b) N-(4-Biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-Dimethylaminopyridine (5 mg) was added, and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1N HCl (2*50 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography using 8:2, hexanes/ethyl acetate, to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide.

Reference： [1]Patent: US5464853,1995,A

54
[ 1623-93-4 ]
[ 33084-49-0 ]
[ 166964-10-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dmap; In pyridine; ethyl acetate;	(b) N-(4-Biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-Dimethylaminopyridine (5 mg) was added, and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1N HCl (2*50 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography using 8:2, hexanes/ethyl acetate, to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide.
60%	With dmap; In pyridine; ethyl acetate;	(a) N-(4-biphenylsulfonyl)-N-(4-Bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-(Dimethyl)aminopyridine (5 mg) was added and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1N HCl (2*50 ml) and the organic phase was dried: over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product which was purified by column chromatography using 8:2, hexanes/ethyl acetate to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-Bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide.

Reference： [1]Patent: US5571821,1996,A
[2]Patent: US5571821,1996,A

55
[ 7335-06-0 ]
[ 1623-93-4 ]
1-([1,1'-biphenyl]-4-ylsulfonyl)pyrrolidine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 2715 - 2720

56
[ 81-64-1 ]
[ 1623-93-4 ]
1,4-bis(1,1'-biphenyl-4-sulfonato)-9,10-anthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate In acetone at 60℃;	1.1; 2.1; 3.1 (1) Preparation of 1,4-bis(1,1'-biphenyl-4-sulfonate)-9,10-anthraquinone (C01) It was added 1,4-dihydroxy-anthraquinone in a glass flask0.5g (2mmol),Excess 4-biphenyl sulfonyl chloride 1.2g,Anhydrous potassium carbonate 0.5g,Then add 20 mL of anhydrous acetone,The reaction is refluxed in an oil bath at 60 ° C,TLC monitors the response throughout the process,After the reaction,Add appropriate amount of ice water to quench the reaction.The pale yellow product was filtered and purified by silica gel column chromatography.Eluent: (dichloromethane: petroleum ether = 1:2) to give a pale yellow target compound.The yield was 74%.

Reference： [1]Current Patent Assignee: GUANGXI UNIVERSITY - CN109608369, 2019, A Location in patent: Paragraph 0041-0043; 0074-0076; 0107-0109

57
[ 36216-80-5 ]
[ 1623-93-4 ]
N-(benzo[d]isoxazol-3-yl)-[1,1-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50 mg	With pyridine; at 20℃; for 80h;	A mixture of <strong>[36216-80-5]benzo[d]isoxazol-3-amine</strong> and a sulfonyl chloride in pyridine (1 ml.) was stirred at room temperature for 16 hours when a second portion of benzenesulfonyl chloride was added and stirred for an additional 64 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration and purified either by preparative mass-directed HPLC (up to 50 mg of crude material) or by silica gel column chromatography (0-40% EtOAc/petroleum benzine 40-60 C) to give the desired product. See Table C for reaction components and amounts used as well as purification conditions.

Reference： [1]Patent: WO2019/243491,2019,A1 .Location in patent: Page/Page column 136

58
[ 118863-62-0 ]
[ 1623-93-4 ]
1-([1,1-biphenyl]-4-ylsulfonyl)-3-(4-bromophenyl)-1H-1,2,4-triazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 8270 - 8280

59
[ 28989-50-6 ]
[ 1623-93-4 ]
N-(4-(thiophen-2-yl)thiazol-2-yl)-[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With pyridine In dichloromethane at -5℃; for 72h;

Reference： [1]Meşeli, Tuǧba; Doǧan, Şengül Dilem; Gündüz, Miyase Gözde; Kökbudak, Zülbiye; Skaro Bogojevic, Sanja; Noonan, Theresa; Vojnovic, Sandra; Wolber, Gerhard; Nikodinovic-Runic, Jasmina [New Journal of Chemistry, 2021, vol. 45, # 18, p. 8166 - 8177]

60
[ 340-05-6 ]
[ 1623-93-4 ]
C₂₀H₁₅F₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃; for 12h;

Reference： [1]Chen, Lei; Li, Xiong; Li, Yue; Lian, Zhong; Sun, Haotian; Xiong, Baojian; Xu, Jie [Organic Letters, 2020, vol. 22, # 23, p. 9263 - 9268]

61
[ 1009101-70-5 ]
[ 1623-93-4 ]
N-((1H-1,2,3-triazol-5-yl)methyl)biphenyl-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	In pyridine at 20℃; for 12h;	1.D Step D: N-((lH-1.2.3-triazol-5-yl)methyl)biphenyl-4-sulfonamide: Biphenyl-4-sulfonyl chloride (80 mg, 0.32 mmol) was added to a solution of (lH-l,2,3-triazol-5- yl)methanamine hydrochloride (45 mg, 0.33 mmol) in pyridine (3.0 mL). After stirring for 12 hours at ambient temperature, the mixture was partitioned between dilute aqueous HCl and DCM. The separated DCM layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting solid was dissolved in isopropyl acetate (3 mL) with heating at 600C, and then allowed to cool to ambient temperature with stirring to give a white crystalline precipitate. The solid was filtered off and air-dried to give 17 mg (15%) of the title compound. MS APCI (-) m/z 313 detected. 1H NMR (400 MHz, DMSO-d6) δ 8.14 (m, IH), 7.81-7.37 (m, 10H), 4.07 (m, 2H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2008/24784, 2008, A1 Location in patent: Page/Page column 19

62
[ 1623-93-4 ]
[ 1426551-76-9 ]
[ 2716851-80-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	6 (6-(biphenyl-4-ylsulfonamido)hexyl)triphenylphosphonium bromide To a stirred solution of ((6-Ammoniohexyl)triphenylphosphonium) bromide (175 mg 0.39 mmol) and Et3N (120 mg, 1.20 mmol) in 10 ml CH2CI2, biphenyl-4-sulfonyl chloride(100 mg 0.39 mmol) was added slowly at 0 °C, and stirring was continued for 6h at room temperature. Completion of the reaction was confirmed by TLC. The reaction mixture was quenched with cold water, and the product was extracted with CH2CI2. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated at reduced pressure. The crude product was purified by flash column chromatography to yield white color solid (169 mg yield 65%).The product was confirmed by LC-MS, [M+H]+ 578.

Reference： [1]Current Patent Assignee: UNIVERSITY OF PENNSYLVANIA; WISTAR INSTITUTE - WO2021/202540, 2021, A1 Location in patent: Page/Page column 67; 75; 76-77

63
[ 1623-93-4 ]
[ 36565-68-1 ]
C₁₆H₁₈BrNO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In dichloromethane at 0℃;

Reference： [1]Zheng, Yu; Lu, Weidong; Xie, Zhenzhen; Chen, Kai; Xiang, Haoyue; Yang, Hua [Organic Letters, 2022, vol. 24, # 29, p. 5407 - 5411]

64
[ 13189-98-5 ]
[ 1623-93-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydroxide In lithium hydroxide monohydrate at 20℃; Cooling with ice;	5 Example 5: synthesis of compound 1e Dissolve fodosteine (1.01g, 0.006mol) in 30ml of water, add sodium hydroxide (0.60g, 0.015mol) and stir to dissolve, add p-phenylbenzenesulfonyl chloride (1.1mL, 0.006mol) under ice bath conditions , transfer to room temperature after the addition of samples, after the reaction is complete, the reaction solution is acidified to pH=2 with 2mol/L hydrochloric acid, a white solid is precipitated, the white solid is collected by filtration and slurried with ethyl acetate, then filtered and dried to obtain a white solid 1e , the yield is 58%.

Reference： [1]Current Patent Assignee: SICHUAN GUOKANG PHARMACEUTICAL - CN114957064, 2022, A Location in patent: Paragraph 0042; 0052-0053

65
[ 1623-93-4 ]
[ 58-39-9 ]
[ 2912518-09-1 ]

Yield	Reaction Conditions	Operation in experiment
41 %	With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Sun, Gang; Liu, Xin; Li, Jing; Yang, Jian-Xin; Xie, Jun-Kai; Wen, Xiaoan; Sun, Hongbin; Xu, Qing-Long [New Journal of Chemistry, 2023, vol. 47, # 10, p. 4746 - 4751]

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Code	Phrase
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P321
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P342	If experiencing respiratory symptoms:
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P378
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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.
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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.
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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
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Code	Phrase
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H304	May be fatal if swallowed and enters airways
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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
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H332	Harmful if inhaled
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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

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[ 1623-93-4 ] Synthesis Path-Upstream 1~4

[ 1623-93-4 ] Synthesis Path-Downstream 1~65

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Aryls

Sulfonyl Chlorides

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[ 1623-93-4 ]