[ CAS No. 63555-50-0 ] {[proInfo.proName]}

Name: 63555-50-0|Methyl 3-(chlorosulfonyl)benzoate|96%
Brand: Ambeed
SKU: A409263
Price: 11.0 USD
Availability: InStock
Rating: 90 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

DV 2D 3D

3d Animation Molecule Structure of 63555-50-0

Structure of 63555-50-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 63555-50-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 63555-50-0 ]

SDS Specification

Alternatived Products of [ 63555-50-0 ]

Product Details of [ 63555-50-0 ]

CAS No. :	63555-50-0	MDL No. :	MFCD06408800
Formula :	C₈H₇ClO₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SQIBNKUEUWGZBH-UHFFFAOYSA-N
M.W :	234.66	Pubchem ID :	113339
Synonyms :

Calculated chemistry of [ 63555-50-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.8
TPSA :	68.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	2.24
Log Po/w (WLOGP) :	2.48
Log Po/w (MLOGP) :	1.43
Log Po/w (SILICOS-IT) :	1.22
Consensus Log Po/w :	1.86

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.83
Solubility :	0.351 mg/ml ; 0.0015 mol/l
Class :	Soluble
Log S (Ali) :	-3.32
Solubility :	0.112 mg/ml ; 0.000478 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.02
Solubility :	0.223 mg/ml ; 0.000951 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.98

Safety of [ 63555-50-0 ]

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:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 63555-50-0 ]

* 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 [ 63555-50-0 ]
Downstream synthetic route of [ 63555-50-0 ]

[ 63555-50-0 ] Synthesis Path-Upstream 1~10

1
[ 63555-50-0 ]
[ 7311-93-5 ]

Reference： [1] Patent: WO2013/96744, 2013, A1,

2
[ 67-56-1 ]
[ 4052-92-0 ]
[ 63555-50-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 13 h;	Reference Example 21 Synthesis of 3-methoxycarbonylbenzenesulfonyl chloride To a solution of 3-chlorocarbonylbenzenesulfonyl chloride (5.0g, 21mmol) in THF (100ml) was added methanol 1.7ml (42mmol) and the mixture was stirred at room temperature for 13 hours. After the reaction was completed, the resultant was concentrated under reduced pressure to give 5.14g (21mmol) of the titled compound as a pale purple solid. Yield: 100percent. ¹H NMR (CDCl₃) δ 8.70 (1H, dd, J = 1.4, 1.9 Hz), 8.42 (1H, dt, J = 1.4, 7.9 Hz), 8.22 (1H, ddd, J = 1.2, 1.9, 7.9 Hz), 7.74(1H, t, J = 7.9 Hz), 4.00 (3H, s).
92%	With pyridine In dichloromethane at 10 - 35℃; for 2 h;	Reference Example 122 Methyl 3-(chlorosulfonyl)benzoate A solution (20 mL) of 3-(chlorosulfonyl)benzoyl chloride (2.4 g) in dichloromethane was cooled to 0°C, and pyridine (791 mg) and methanol (320 mg) were added. The reaction mixture was stirred at room temperature for 2 hr, and the solvent was evaporated under reduced pressure. The residue was filtrated, washed with a mixed solvent of ethyl acetate and isopropyl ether, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a colorless oil (yield 2.17 g, 92percent). ¹H-NMR (CDCl₃)δ: 3.99 (3H, s), 7.74 (1H, t, J=8.1 Hz), 8.21-8.24 (1H, m), 8.39-8.43 (1H, m), 8.69-8.70 (1H, m).

Reference： [1] Patent: EP1728793, 2006, A1, . Location in patent: Page/Page column 127
[2] Patent: WO2006/36024, 2006, A1, . Location in patent: Page/Page column 156
[3] Patent: EP2336107, 2015, B1, . Location in patent: Paragraph 0296
[4] Recueil des Travaux Chimiques des Pays-Bas, 1921, vol. 40, p. 726
[5] Patent: WO2007/23186, 2007, A1, . Location in patent: Page/Page column 49
[6] Patent: WO2009/5998, 2009, A1, . Location in patent: Page/Page column 209-210
[7] Patent: CN107540636, 2018, A, . Location in patent: Paragraph 0223-0225

3
[ 4518-10-9 ]
[ 63555-50-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With hydrogenchloride; acetic acid; sodium nitrite In water at -10 - -5℃; for 1.5 h; Stage #2: With sulfur dioxide; copper(l) chloride In water; acetic acid at 5 - 15℃; for 1 h;	To a mixture of conc. HCl (16 mL) and glacial acetic acid (5 mL), was added methyl 3-aminobenzoate (7.40g, 49 mmol). The flask was placed in a dry ice-ethanol bath and the temperature of the mixture lowered to -10°C. A solution of sodium nitrite (3.7 g, 53 mmol) in water (5.4 mL) was added dropwise, at such a rate so that the temperature did not exceed -5°C. The mixture was left stirring at -10°C to -5°C for 1h 30 min. SO₂ was introduced into acetic acid (49 mL) by a tube immersed below the surface, over a period of 30 min. CuCl (1.35 g, 13.6 mmol) was added and SO₂ was kept bubbling for a further h. The mixture was cooled with ice to 5°C and the diazonium salt was added dropwise so as to maintain the temperature. After the addition the mixture was allowed to warm to 15°C and stirred for 1 h. Ice was added and the mixture stirred until it melted, extracted with ether (3 x 120 mL) washed with NaHCO₃ (100 mL) dried (MgSO₄) and the solvent evaporated in vacuo to give 31 (7.7 g, 67percent) as orange plates (mp 64-66°C).
42%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With sulfur dioxide; acetic acid; copper(l) chloride In water at 20℃; for 3 h;	A mixture of METHYL-4-AMINOBENZOATE (1.0 g, 6.6 MMOL) in concentrated hydrochloric acid (15 mL) was maintained AT 0° C AS A SOLUTION of sodium nitrite (1.12 g, 13.2 mmol) in water (4 mL) was added dropwise with stirring. This reaction was maintained at 0° C for 30 minutes. In a separate flask, a mixture of copper (L) chloride (89 mg, 0.66 MMOL) and glacial acetic acid (9.9 mL) cooled to below room temperature was saturated with gaseous sulfur dioxide for several minutes. The mixture containing the crude diazonium salt was then added to the second flask portionwise with extreme caution. The mixture was allowed to stir at ambient temperature for 3h before being poured onto crushed ice. The resulting solid was filtered. Additional product was recovered by extraction of the aqueous filtrate with ethyl acetate. The combined yield of methyl 4- (CHLOROSULFONYL) benzoate is 0.65 g. (42percent).

Reference： [1] ChemSusChem, 2017, vol. 10, # 1, p. 151 - 155
[2] Tetrahedron, 2015, vol. 71, # 38, p. 6701 - 6719
[3] Patent: WO2004/48349, 2004, A1, . Location in patent: Page 67

4
[ 2565-10-8 ]
[ 63555-50-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With thionyl chloride In N,N-dimethyl-formamide at 80℃;	The intermediate 8 (10 g, 42 mmol) was dissolved in SOCl₂ (180 mL) followed by addition of 0.2 mL of DMF. Then the solution was refluxed at 80 °C for 4-6 h. After the reaction was completed, the solution was cooled and half of the solvent was distilled off. The mixture of ice and water was added slowly into the solution at 0-5 °C. After it was completely quenched, the solution was filtered and the precipitate was dried under vacuum to afford compound 9, a white solid (8.0 g, 85percent yield).

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 282 - 291

5
[ 4052-92-0 ]
[ 63555-50-0 ]

Reference： [1] Patent: EP1803709, 2007, A1,

6
[ 67-56-1 ]
[ 4025-64-3 ]
[ 63555-50-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 212 - 221
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 3, p. 442 - 454

7
[ 4025-64-3 ]
[ 63555-50-0 ]

Reference： [1] Patent: US6177466, 2001, B1,
[2] Patent: CN107540636, 2018, A,

8
[ 99769-19-4 ]
[ 63555-50-0 ]

Reference： [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641

9
[ 17625-03-5 ]
[ 63555-50-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 282 - 291

10
[ 186581-53-3 ]
[ 4025-64-3 ]
[ 63555-50-0 ]

Reference： [1] Magnetic Resonance in Chemistry, 1989, vol. 27, # 6, p. 585 - 591

[ 63555-50-0 ] Synthesis Path-Downstream 1~88

1
[ 186581-53-3 ]
[ 4025-64-3 ]
[ 63555-50-0 ]

Reference： [1]Magnetic Resonance in Chemistry,1989,vol. 27,p. 585 - 591

2
[ 39662-63-0 ]
[ 63555-50-0 ]
[ 111711-77-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1991,vol. 26,p. 403 - 413

3
[ 67-56-1 ]
[ 4025-64-3 ]
[ 63555-50-0 ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 103 - 121
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 442 - 454

4
[ 63555-50-0 ]
[ 926291-90-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 442 - 454

5
[ 63555-50-0 ]
[ 926292-02-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 442 - 454

6
[ 63555-50-0 ]
[ 926292-01-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 442 - 454

7
[ 63555-50-0 ]
C₃₇H₅₀N₂O₆S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 442 - 454

8
[ 63555-50-0 ]
(E)-3-[1-(4-cetyloxy-3-methoxyphenyl)-1-phenylmethylene]-sulfohydrazono-benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 442 - 454

9
4-[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenylamine [ No CAS ]
[ 63555-50-0 ]
methyl 3-[(4-[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)amino]sulfonyl}benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine; In 1,4-dioxane; at 20℃;	A mixture of 4-[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2- methylphenylamine (85 mg, 217 PMOL), METHYL 4-(CHLOROSULFONYL) benzoate (51 mg, 217 LIMON), pyridine (52 muL, 651 mumol), and dioxane (1.1 mL) was stirred at ambient temperature overnight. The reaction was condensed and the resulting residue chromatographed on silica gel eluting with 50% ETHYL ACETATE/HEXANES. YIELD = 119 mg (93%) of methyl 3-[(4-[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4- yl]methoxy}-2-methylphenyl)amino]sulfonyl} benzoate.

Reference： [1]Patent: WO2004/48349,2004,A1 .Location in patent: Page 68

10
[ 4518-10-9 ]
[ 63555-50-0 ]

Yield	Reaction Conditions	Operation in experiment
67%		To a mixture of conc. HCl (16 mL) and glacial acetic acid (5 mL), was added methyl 3-aminobenzoate (7.40g, 49 mmol). The flask was placed in a dry ice-ethanol bath and the temperature of the mixture lowered to -10C. A solution of sodium nitrite (3.7 g, 53 mmol) in water (5.4 mL) was added dropwise, at such a rate so that the temperature did not exceed -5C. The mixture was left stirring at -10C to -5C for 1h 30 min. SO2 was introduced into acetic acid (49 mL) by a tube immersed below the surface, over a period of 30 min. CuCl (1.35 g, 13.6 mmol) was added and SO2 was kept bubbling for a further h. The mixture was cooled with ice to 5C and the diazonium salt was added dropwise so as to maintain the temperature. After the addition the mixture was allowed to warm to 15C and stirred for 1 h. Ice was added and the mixture stirred until it melted, extracted with ether (3 x 120 mL) washed with NaHCO3 (100 mL) dried (MgSO4) and the solvent evaporated in vacuo to give 31 (7.7 g, 67%) as orange plates (mp 64-66C).
42%		A mixture of METHYL-4-AMINOBENZOATE (1.0 g, 6.6 MMOL) in concentrated hydrochloric acid (15 mL) was maintained AT 0 C AS A SOLUTION of sodium nitrite (1.12 g, 13.2 mmol) in water (4 mL) was added dropwise with stirring. This reaction was maintained at 0 C for 30 minutes. In a separate flask, a mixture of copper (L) chloride (89 mg, 0.66 MMOL) and glacial acetic acid (9.9 mL) cooled to below room temperature was saturated with gaseous sulfur dioxide for several minutes. The mixture containing the crude diazonium salt was then added to the second flask portionwise with extreme caution. The mixture was allowed to stir at ambient temperature for 3h before being poured onto crushed ice. The resulting solid was filtered. Additional product was recovered by extraction of the aqueous filtrate with ethyl acetate. The combined yield of methyl 4- (CHLOROSULFONYL) benzoate is 0.65 g. (42%).

Reference： [1]ChemSusChem,2017,vol. 10,p. 151 - 155
[2]Tetrahedron,2015,vol. 71,p. 6701 - 6719
[3]Patent: WO2004/48349,2004,A1 .Location in patent: Page 67

11
[ 363-81-5 ]
[ 63555-50-0 ]
3-[N-(2,4,6-Trifluorophenyl)sulfamoyl]-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.2%	With pyridine; In 1,1-dichloroethane; dichloromethane;	(a) 3-[N-(2,4,6-Trifluorophenyl)sulfamoyl]-benzoic acid methyl ester 2.35 g (10 mmol) of <strong>[63555-50-0]3-chlorosulfonylbenzoic acid methyl ester</strong> is suspended in 30 ml of dichloromethane with exclusion of moisture, the suspension is cooled to -5 C and at this temperature a solution of 1.47 g (10 mmol) of 2,4,6-trifluoroaniline and 1 ml of pyridine in 20 ml of dichloromethane is instilled. When the instillation is completed, it is allowed to come to room temperature and is stirred for 12 more hours. The resulting precipitate is suctioned off and extracted with ether. The ether extract and filtrate together are concentrated by evaporation and the residue is dissolved in dichloroethane and chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane. 2.8 g (8.12 mmol)= 81.2% of the theoretical yield is obtained as an amorphous product.

Reference： [1]Patent: US5130119,1992,A

Yield	Reaction Conditions	Operation in experiment
		As specific examples of the compounds of the formula (IV) there may be mentioned: benzenesulfonylchloride, 3-methoxycarbonylbenzenesulfonylchloride, p-toluenesulfonylchloride, and methanesulfonylchloride.

13
[ 4025-64-3 ]
[ 63555-50-0 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 7 3-(Methoxycarbonyl)benzenesulfonyl chloride The title compound was obtained by the same procedure as a series of reaction of reference example 6, using 3-carboxybenzenesulfonyl chloride instead of 4-carboxybenzenesulfonyl chloride.

Reference： [1]Patent: US6177466,2001,B1
[2]Patent: CN107540636,2018,A
[3]Patent: CN109232442,2019,A

14
[ 866268-43-1 ]
[ 63555-50-0 ]
[ 866268-90-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In tetrahydrofuran; at 20℃; for 1.5h;	Reference Example 22; Synthesis of 2-butoxy-8-methoxy-9-[4-(3-methoxycarbonylbenzenesulfonamide)butyl]adenine; [Show Image] To a solution of 2-butoxy-8-methoxy-9-(4-aminobutyl)adenine (440mg, 1.4mmol) obtained in Reference Example 20 in THF (20ml) were added 3-chlorocarbonylbenzenesulfonyl chloride (502mg, 2.1mmol) obtained in Reference Example 22 and triethylamine (312mul, 2.3mmol) and the mixture was stirred at room temperature for 1.5 hour. To the resultant was added water, and the mixture was concentrated under reduced pressure and purification by silica gel column chromatography to give 724mg (1.4mmol)of the titled compound as a white solid. Yield: 100 %. 1H NMR (DMSO-d6) delta 8.30 (1H, dd, J = 1.4, 1.7 Hz), 8.15 (1H, ddd, J = 1.3, 1.4, 7.9 Hz), 8.00 (1H, ddd, J = 1.3, 1.7, 7.9 Hz), 7.79 (1H, t, J = 5.8 Hz), 7.73 (1H, t, J = 7.9 Hz), 6.81 (2H, brs), 4.13 (2H, t, J = 6.6 Hz), 4.02 (3H, s), 3.90 (3H, s), 3.77 (1H, t, J = 6.7 Hz), 2.75 (1H, dt, J = 5.8, 6.6 Hz), 1.65-1.60 (4H, m), 1.42-1.37 (2H, m), 1.27-1.22 (2H, m), 0.89 (3H, t, J = 7.4 Hz).

Reference： [1]Patent: EP1728793,2006,A1 .Location in patent: Page/Page column 127

15
[ 56448-22-7 ]
[ 63555-50-0 ]
[ 881676-67-1 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 225 Methyl 3-[(4-formyl-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoate Using 5-phenyl-1H-pyrrole-3-carbaldehyde (1.32 g), sodium hydride (60% in oil, 444 mg), 15-crown-5 (2.04 g) and methyl 3-(chlorosulfonyl)benzoate (2.17 g), a procedure as in Reference Example 219 was performed to give the title compound as a pale-yellow oil (yield 1.96 g, 69%). 1H-NMR (CDCl3)delta: 3.92 (3H, s), 6.57 (1H, d, J=2.1 Hz), 7.12-7.15 (2H, m), 7.26-7.32 (2H, m), 7.37-7.49 (3H, m), 7.96-7.97 (1H, m), 8.13-8.14 (1H, m), 8.18-8.22 (1H, m), 9.90 (1H, s).

Reference： [1]Patent: EP1803709,2007,A1

16
[ 4052-92-0 ]
[ 63555-50-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In methanol; dichloromethane;	Reference Example 122 Methyl 3-(chlorosulfonyl)benzoate A solution (20 mL) of 3-(chlorosulfonyl)benzoyl chloride (2.4 g) in dichloromethane was cooled to 0C, and pyridine (791 mg) and methanol (320 mg) were added. The reaction mixture was stirred at room temperature for 2 hr, and the solvent was evaporated under reduced pressure. The residue was filtrated, washed with a mixed solvent of ethyl acetate and isopropyl ether, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1?4:1) to give the title compound as a colorless oil (yield 2.17 g, 92%). 1H-NMR (CDCl3)delta: 3.99 (3H, s), 7.74 (1H, t, J=8.1 Hz), 8.21-8.24 (1H, m), 8.39-8.43 (1H, m), 8.69-8.70 (1H, m).

Reference： [1]Patent: EP1803709,2007,A1

17
[ 1215-59-4 ]
[ 63555-50-0 ]
[ 1097777-81-5 ]

Yield	Reaction Conditions	Operation in experiment
36%		To a 3 -neck round bottom flask was added sodium hydride (60% dispersion in oil) (0.143 g, 3.58 mmol). The sodium hydride was washed with hexanes and the solid was cooled in an ice-water bath. To the washed sodium hydride was slowly added a solution of 5-benzyloxyindole (0.515 g, 2.31 mmol) in N,N-dimethylformamide (5 mL) with stirring under a nitrogen atmosphere. The reaction mixture was stirred with cooling for 10 min. To the cold reaction mixture was added a solution of methyl 3- (chlorosulfonyl)benzoate (0.762 g, 3.2 mmol) in N,N-dimethylformamide (5 mL). The ice-water bath was removed and the reaction mixture was stirred overnight at room temperature. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give a brown-orange liquid. The crude product was purified by flash chromatography over silica with a hexanes:ethyl acetate gradient (100:0 to 60:40) to <n="212"/>give 0.352 g (36%) of methyl 3-({5-[(phenylmethyl)oxy]-lH-indol-l- yl}sulfonyl)benzoate as a colorless oil.1H NMR (400 MHz, CDCl3): delta 8.51 (m, IH), 8.18 (d, J = 8 Hz, IH), 8.00 (d, J = 8 Hz, IH), 7.89 (d, J = 9 Hz, IH), 7.52 (m, 2H), 7.30-7.43 (m, 5H), 7.03 (m, 2H), 6.60 (d, J = 4 Hz, IH), 5.05 (s, 2H), 3.93 (s, 3H). ES-LCMS m/z 444 (M + Na)+.

Reference： [1]Patent: WO2009/5998,2009,A1 .Location in patent: Page/Page column 210-211
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4733 - 4739

18
[ 1187966-51-3 ]
[ 63555-50-0 ]
[ 1187966-56-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;	3-[(2,3-Diaza-spiro[4.41non-3-en-2-yl)-ethylamino-methylene1-sulfamoyl)-benzoic acid methyl ester; To a solution of 4.07 g <strong>[63555-50-0]3-chlorosulfonyl-benzoic acid methyl ester</strong> in 150 ml. DCM were added 17,69 ml. (6.0 equiv.) DiPEA and 4.00 g (1.0 equiv.) N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2- carboxamidine. The reaction mixture was stirred overnight at room temperature under N2 atmosphere, and extracted with water. The organic phase was dried over Na2SO4 and evaporated, and the residue was purified by automated flash chromatography (EtOAc/PA 1 : 1 ) to give 4.8O g (71%) of a yellow solid. 1H NMR (400 MHz, CDCI3) delta 1.16 (t, J=8 Hz, 3H), 1.62-1.86 (m, 8H), 3.42-3.53 (m, 2H), 3.87 (s, 2H), 3.95 (s, 3H), 6.83 (s, 1 H), 6.83-6.95 (broad peak, 1 H), 7.56 (t, J=8 Hz, 1 H), 8.13-8.18 (m, 2H), 8.61 (s, 1 H).

Reference： [1]Patent: WO2009/115515,2009,A1 .Location in patent: Page/Page column 56

19
[ 63555-50-0 ]
[ 79456-26-1 ]
[ 1254207-51-6 ]

Yield	Reaction Conditions	Operation in experiment
45%		Step- 1 : Methyl 3-fN-G-chloro-5-alpharifluoromethvDpyridin-2-vDsulfamovDbenzoateTo a suspension of NaH (60% in oil, 146 mg, 3.82 mmol) in THF (30 mL) was added 3-chloro-5-(trifluoromethyl)pyridin-2-amine (500 mg, 2.54 mmol) at 0 0C and stirred at room temperature for 1 h. Then, to the mixture was added methyl 3-(chlorosulfonyl)benzoate (597 mg, 2.54 mmol) at 0 0C and stirred at room temperature for 2 hrs. The mixture was acidified by 2 M aqueous HCl solution, extracted with EtOAc (2 times), dried over Na2SO4, filtered and concentrated. The residue was applied to a silica gel column chromatography and eluted with hexane/EtOAc = 1/1 to furnish 455 mg (45% yield) of the titled compound as a pale yellow solid;[0451] 1H-NMR (300 MHz, CDCI3) delta 8.82 (1 H, s), 8.45-8.36 (2H, m), 8.29 (1 H, d, J = 8.1 Hz), 7.84(1 H, s), 7.65 (1 H, t, J = 8.1 Hz), 3.97 (3H, s), a signal due to SO2NH was not observed; [0452] LC-MS (Method A) m/z: M+l obs 395.15, tR = 3.00 min.

Reference： [1]Patent: WO2010/125831,2010,A1 .Location in patent: Page/Page column 66
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5364 - 5368

20
[ 63555-50-0 ]
tert-butyl 3-aminopropanoate hydrochloride [ No CAS ]
[ 1366068-20-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of methyl 3-(chlorosulfonyl)benzoate (5.0 g, 21.31 mmol) in pyridine (50 ml), was added dropwise a solution of tert-butyl 3-aminopropanoate hydrochloride (5.11 g, 23.44 mmol) in pyridine (10 ml) at 0 C. The resulting solution was allowed to warm to RT and stirred for 4 h. 1N HCl (50 ml) was added to the reaction mixture and the aqueous phase was separated and extracted with DCM (3x20 ml). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford a viscous amber oil. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the title compound as a colourless oil. 1H NMR (400 MHz, CDCl3) delta 8.53 (1H, s), 8.27 (1H, d), 8.08 (1H, d), 7.63 (1H, t) 5.38 (1H, t), 3.97 (3H, s), 3.20 (2H, m), 2.48 (2H, t), 1.43 (9H, s).
	In pyridine; at 0 - 20℃; for 4h;	To a stirred solution of methyl 3-(chlorosulfonyl)benzoate (5.0 g, 21.31 mmol) in pyridine (50 ml), was added dropwise a solution of tert-butyl 3-aminopropanoate hydrochloride (5.11 g, 23.44 mmol) in pyridine (10 ml) at 0 C. The resulting solution was allowed to warm to RT and stirred for 4 h. 1N HCl (50 ml) was added to the reaction mixture and the aqueous phase was separated and extracted with DCM (3×20 ml). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford a viscous amber oil. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the title compound as a colourless oil. 1H NMR (400 MHz, CDCl3) delta 8.53 (1H, s), 8.27 (1H, d), 8.08 (1H, d), 7.63 (1H, t) 5.38 (1H, t), 3.97 (3H, s), 3.20 (2H, m), 2.48 (2H, t), 1.43 (9H, s).

Reference： [1]Patent: US2012/71479,2012,A1 .Location in patent: Page/Page column 29
[2]Patent: US2014/113914,2014,A1 .Location in patent: Paragraph 0261

21
[ 1366068-12-3 ]
[ 63555-50-0 ]
[ 1366068-16-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 20℃; for 2h;	A solution of 1-aminomethyl-cyclobutanecarboxylic acid tert-butyl ester (step 2) (1.47 g, 7.38 mmol) in DCM (40 ml) was treated with TEA (2.57 ml, 18.44 mmol) followed by methyl 3-(chlorosulfonyl)benzoate (1.91 g, 8.11 mmol) and DMAP (0.09 g, 0.74 mmol). The mixture was stirred at RT for 2 h and then partitioned between DCM and water. The aqueous portion was extracted with DCM and the combined organic extracts were washed with 0.1N HCl, brine, dried over MgSO4 and concentrated in vacuo. Purification of the resulting oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded the title compound as a colourless oil; 1H NMR (400 MHz, CDCl3) delta 8.56 (1H, s), 8.27 (1H, d), 8.08 (1H, d), 7.64 (1H, t), 5.21 (1H, br t), 3.98 (3H, s), 3.20 (2H, d), 2.37 (2H, m), 1.96 (4H, m), 1.46 (9H, s).
	With dmap; triethylamine; In dichloromethane; at 20℃; for 2h;	A solution of 1-aminomethyl-cyclobutanecarboxylic acid tert-butyl ester (step 2) (1.47 g, 7.38 mmol) in DCM (40 ml) was treated with TEA (2.57 ml, 18.44 mmol) followed by methyl 3-(chlorosulfonyl)benzoate (1.91 g, 8.11 mmol) and DMAP (0.09 g, 0.74 mmol). The mixture was stirred at RT for 2 h and then partitioned between DCM and water. The aqueous portion was extracted with DCM and the combined organic extracts were washed with 0.1N HCl, brine, dried over MgSO4 and concentrated in vacuo. Purification of the resulting oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded the title compound as a colourless oil; 1H NMR (400 MHz, CDCl3) delta 8.56 (1H, s), 8.27 (1H, d), 8.08 (1H, d), 7.64 (1H, t), 5.21 (1H, br t), 3.98 (3H, s), 3.20 (2H, d), 2.37 (2H, m), 1.96 (4H, m), 1.46 (9H, s).

Reference： [1]Patent: US2012/71479,2012,A1 .Location in patent: Page/Page column 29
[2]Patent: US2014/113914,2014,A1 .Location in patent: Paragraph 0258

22
[ 63555-50-0 ]
tert-butyl 3-aminopropanoate hydrochloride [ No CAS ]
[ 1366067-47-1 ]

Reference： [1]Patent: US2012/71479,2012,A1
[2]Patent: US2014/113914,2014,A1

23
[ 110-89-4 ]
[ 63555-50-0 ]
[ 415712-10-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃;	General procedure: To a solution of Compound 1 (10 mmol) in CH2CI2 (50 mL) was added amine (10 mmol) and TEA (11 mmol), and stirred at rt overnight. The mixture was washed with 1 N HC1 and saturated NaHC03, and concentrated in vacuo. The residue was purified by chromatography to give the desire product
	In dichloromethane; for 2h;Cooling with ice;	To a stirred solution of 3-Chlorosulfonyl methyl benzoate (300 mg, 1.28 mmol) in DCM (10 mL), piperidine (3.84 mol, 3eq) was added drop wise under ice cooling and the mixture was stirred for 2hours. HCl IN (8ml) was added thereto. After separation, the organic phase was washed with brine (8 mL) and dried (Na2S04). The solvent was evaporated and the resulting compound was used directly without further purification. (Yield = 91%). NMR (400MHZ, CDCI3) : 8.37 (1H, s), 8.24 (2H, dd), 7.92 (1H, d), 7.60 (1H, t), 2.99 (1H, m), 1.64 (4H, m), 1.41 (2H, m).

Reference： [1]Patent: WO2013/96744,2013,A1 .Location in patent: Page/Page column 234
[2]Patent: WO2016/16370,2016,A1 .Location in patent: Page/Page column 42

24
[ 63555-50-0 ]
[ 1004093-11-1 ]

Reference： [1]Patent: WO2013/96744,2013,A1

25
[ 63555-50-0 ]
[ 7311-93-5 ]

Reference： [1]Patent: WO2013/96744,2013,A1

26
[ 1448038-87-6 ]
[ 63555-50-0 ]
[ 1448038-93-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 20℃;	General procedure: A mixture of indoline 4, 2 eq. of sulfonyl chloride and 6 eq. of pyridine is stirred at rt for 18 - 24 h. The reaction mixture is partitioned between water and dichloromethane, extracted with dichloromethane, the combined organic layers are washed with water, dried with sodium sulfate, concentrated and purified via flash chromatography (SiO2-hexane/ethyl acetate).C.3 was prepared according to GP 4.2 starting from B.3 and methyl 3-{chlorosulfonyl)benzoate (CAS No. [63555-50-0]). 1H-NMR (400MHz, CDCl3): Shift [ppm] = 0.48 (dbr, 1H), 1.10 (tbr, 1H), 2.06 (m, 2H), 2.22 (dbr, 1H), 2.32 (m, 1H), 2.61 (m, 2H), 2.70 (qbr, 1H), 3.96 (s, 3H), 4.38 (m, 1 H), 5.02 - 5.12 (m, 2H), 5.78 (m, 1H), 7.11 (s, 1H), 7.37 (dbr, 1H), 7.53 (m, 2H), 7.95 (dbr, 1H), 8.23 (dbr, 1H), 8.49 (br. s.). UPLC-MS (ESI+): [M + H]+ = 522 / 524 (Br isotope pattern).

Reference： [1]Patent: WO2013/107743,2013,A1 .Location in patent: Page/Page column 44; 53; 54

27
[ 1448038-87-6 ]
[ 63555-50-0 ]
[ 1448039-07-3 ]

Reference： [1]Patent: WO2013/107743,2013,A1

28
[ 63555-50-0 ]
[ 371-40-4 ]
[ 1286550-87-5 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20℃;	General procedure: The residue mentioned above was dissolved in toluene, followed by added catalytic amounts of DMF, dropwise added SOCl2 at 0 C. After that, the reaction mixture was heated to 80 C and stirred for 12 h. The solvent was evaporated to dryness, and the residue was dissolved in toluene. The phenylamine dissolved in toluene (30 ml) was dropwise added to the resulting solution, and then the reaction mixture was stirred overnight. Then the mixture was filtered, and the filtration was washed by water for three times, which was further purified by recrystallization from toluene to give the title compound 34a as white solid (7.83g, 67% in three step).
	In toluene; at 25℃; for 18h;Inert atmosphere;	To a solution of Compound 10 (1.62 mL, 17.05 mmol) in toluene (10 mL), Compound 11 (2.0 g, 8.5 mmol) in toluene (20 mL) was added dropwise to the solution for 10 min. The reaction was stirred at 25 C under nitrogen atmosphere. After the reaction was completed, the mixture filtered, and the solvent was removed under reduced pressure. Compound 12 was obtained without further purification. To a solution of anhydrous LiCl (0.74 g, 17.46 mmol) in dry THF (16 mL), KBH4 (0.94 g, 17.43 mmol) was added to the solution. Compound 12 (2.64 g,8.5 mmol) in dry THF (5 mL) was added dropwise for 10 min. The reactionwas refluxed at 70 C under nitrogen atmosphere. After the reaction was completed, the mixture filtered, and the solvent was removed under reduced pressure. Then, the mixture was dissolved inacetone (5 mL) and DCM (20 mL). PCC (3.67 g, 17.05 mmol) and 100 A silica gel (6.0 g) was added to the solution. The reaction was stirred at 25 C under nitrogen atmosphere. After the reaction was completed, the mixture was filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (4:1) to give white solid Compound 5e (1.44 g, 5.16 mmol, 60.7% yield for 3 steps).

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10638 - 10641
[2]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1502 - 1506
[3]Bioorganic and Medicinal Chemistry,2020,vol. 28

29
[ 99769-19-4 ]
[ 63555-50-0 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10638 - 10641

30
[ 63555-50-0 ]
[ 53934-78-4 ]
[ 1611455-10-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With triethylamine; In tetrahydrofuran; at 20℃; for 0.5h;	A stirred solution of tert-butyl-2-amino-2-phenylacetate (1.34 g, 6.45 mmol) and methyl 3-(chlorosulfonyl)benzoate (1.53 g, 6.51 mmol) in tetrahydrofuran (15 mL) was added with triethylamine (0.90 mL, 6.45 mmol) in one portion at ambient temperature. The reaction mixture was stirred for 30 minutes, after which time, the reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate (30 mL)and 10% citric acid solution (10 mL). The resulting organic phases were dried over magnesium sulfate and concentrated under reduced pressure to yield a crude solid. The solid was triturated in diethyl ether (5 mL) and cold methanol (5 mL) to yield the title compound as a white solid (1.13 g, 43%).?H NMR (400 MHz, CDC13): oe 8.32 (t, J = 1.9 Hz, 1 H), 8.12 (dt, J = 7.9, 1.5 Hz,1 H), 7.86 (ddd, J = 7.9, 1.9, 1.2 Hz, 1 H), 7.44 (t, J = 7.9 Hz, 1 H), 7.22-7.13 (m, 5 H),5.79 (d, J = 7.6 Hz, 1 H), 5.00 (d, J = 7.7 Hz, 1 H), 3.94 (s, 3 H), 1.26 (s, 9 H). LCMS (Method 2): [M-H] = 404 at 4.12 mm.
43%	With triethylamine; In tetrahydrofuran; at 20℃; for 0.5h;	Methyl 3-[(2-tert-butoxy-2-oxo-1-phenylethyl)sulfamoyl]benzoate (I-22) To a stirred solution of tert-butyl-2-amino-2-phenylacetate (1.34 g, 6.45 mmol) and methyl 3-(chlorosulfonyl)benzoate (1.53 g, 6.51 mmol) in tetrahydrofuran (15 mL) was added triethylamine (0.90 mL, 6.45 mmol) in one portion at ambient temperature. The reaction mixture was stirred for 30 minutes, after which time, the reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate (30 mL) and 10% citric acid solution (10 mL). The resulting organic phases were dried over magnesium sulfate and concentrated under reduced pressure to yield a crude solid. The solid was triturated in diethyl ether (5 mL) and cold methanol (5 mL) to yield the title compound as a white solid (1.13 g, 43%). 1H NMR (400 MHz, CDCl3): delta 8.32 (t, J=1.9 Hz, 1H), 8.12 (dt, J=7.9, 1.5 Hz, 1H), 7.86 (ddd, J=7.9, 1.9, 1.2 Hz, 1H), 7.44 (t, J=7.9 Hz, 1H), 7.22-7.13 (m, 5H), 5.79 (d, J=7.6 Hz, 1H), 5.00 (d, J=7.7 Hz, 1H), 3.94 (s, 3H), 1.26 (s, 9H). LCMS (Method 2): [M-H]=404 at 4.12 min.

Reference： [1]Patent: WO2014/86849,2014,A1 .Location in patent: Page/Page column 80
[2]Patent: US2014/155428,2014,A1 .Location in patent: Paragraph 0463 - 0465

31
[ 120-72-9 ]
[ 63555-50-0 ]
[ 1609171-99-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4009 - 4022

32
[ 63555-50-0 ]
[ 1609171-90-5 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4009 - 4022

33
[ 63555-50-0 ]
[ 1315501-71-3 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4009 - 4022

34
[ 63555-50-0 ]
[ 1609172-00-0 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4009 - 4022

35
[ 63555-50-0 ]
[ 1609172-01-1 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4009 - 4022

36
[ 63555-50-0 ]
C₂₂H₂₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4009 - 4022

37
[ 63555-50-0 ]
[3-(indole-1-sulfonyl)phenyl]methanol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4009 - 4022

38
cis-N-methyl-N-7H-pyrrolo[2,3-d]pyrimidin-4-ylcyclobutane-1,3-diamine hydrochloride [ No CAS ]
[ 63555-50-0 ]
methyl 3-[({cis-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclobutyl}amino)-sulfonyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h;Inert atmosphere;	Step 1: Methyl 3-[({cis-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-cyclobutyl}amino)-sulfonyl]benzoate To a suspension of cis-N-methyl-N-7H-pyrrolo[2,3-d]pyrimidin-4-ylcyclobutane-1,3-diamine hydrochloride (1.8 g, 8.29 mmol) in N,N-dimethylformamide (100 mL) was added portionwise triethylamine (6.7 mL, 49 mmol) at 0 C. Methyl 3-(chlorosulfonyl)benzoate (2.3 g, 9.9 mmol) was added at 0 C. The resulting mixture was stirred at room temperature for 3 hours. The solvent was removed under vacuum. The residue was chromatographed on silica gel eluting with a gradient of methanol in dichloromethane (3% to 10%) to afford the title compound (1.6 g, 47%) as a yellow solid.

Reference： [1]Patent: US2014/243312,2014,A1 .Location in patent: Paragraph 0228

39
[ 63555-50-0 ]
[ 70034-78-5 ]
methyl 3-(N-(4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)butyl)sulfamoyl)benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7136 - 7140

40
[ 63555-50-0 ]
[ 70034-78-5 ]
3-(N-(4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)butyl)sulfamoyl)benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7136 - 7140

41
3-amino-5-chloropyridin-4-ol [ No CAS ]
[ 63555-50-0 ]
methyl 3-[(5-chloro-4-hydroxypyridin-3-yl)sulfamoyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With pyridine; dmap; at 40℃; for 4h;Inert atmosphere;	Toa stirred solution of 3-amino-5-chloropyridin-4-ol (500 mg, 3.46 mmol) inpyridine (3 mL) was added DMAP (10 mg, 0.08 mmol) and methyl3-(chlorosulfonyl)benzoate (812 mg, 3.46 mmol). The reaction was stirred at40C under nitrogen for 4 hrs. The reaction mixture was concentrated in vacuo,diluted in EtOAc (140 mL), the organic layer washed with water (2x100 mL) andwashed with brine. The organic layer was dried over Na2SC>4 andconcentrated in vacuo to afford the title compound as an orange solid (185mg,14%); m/z=342.8, 344.9(MH)+.

Reference： [1]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 65; 66

42
[ 808770-39-0 ]
[ 63555-50-0 ]
methyl 3-[(6-chloro-4-methoxypyridazin-3-yl)sulfamoyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Toa suspension of 6-chloro-4-methoxypyridazin-3-amine (1.00 g, 6.27 mmol) in dryDME (30 mL) was added sodium hydride (60%, 238 mg, 5.85 mmol) and the mixturestirred 5 mins. Methyl 3-(chlorosulfonyl)benzoate (1.47 g, 6.27 mmol) was thenadded and the mixture stirred 1 hr. EtOAc was added (100 mL) followed by 1M HCl(30 mL) and the phases were separated. The organic phase was washed with brine(15 mL), dried ( a2S04), the mixture filtered and thefiltrate evaporated to dryness to afford an off white solid containing thetitle compound (1.84g at 47% purity, 38% yield); m/z=357.8, 359.9 (MH)+.

Reference： [1]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 85

43
[ 63555-50-0 ]
3-[(5-bromo-3-hydroxypyrazin-2-yl)sulfamoyl]benzoic acid [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

44
[ 63555-50-0 ]
methyl 3-[(6-chloro-4-hydroxypyridazin-3-yl)sulfamoyl]benzoate [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

45
[ 63555-50-0 ]
3-[(6-chloro-4-hydroxypyridazin-3-yl)sulfamoyl]benzoic acid [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

46
[ 63555-50-0 ]
3-[(5-chloro-4-hydroxypyridin-3-yl)sulfamoyl]-N,N-diethylbenzamide [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

47
[ 63555-50-0 ]
3-[(5-bromo-3-hydroxypyrazin-2-yl)sulfamoyl]-N,N-diethylbenzamide [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

48
[ 63555-50-0 ]
3-[(6-chloro-4-hydroxypyridazin-3-yl)sulfamoyl]-N,N-diethylbenzamide [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

49
[ 63555-50-0 ]
3-[(5-chloro-4-hydroxypyridin-3-yl)sulfamoyl]benzoic acid [ No CAS ]

Reference： [1]Patent: WO2014/184234,2014,A1

50
[ 63555-50-0 ]
[ 100-46-9 ]
methyl 3-(N-benzylsulfamoyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine; In toluene; at 20℃;	General procedure: To a solution of 10a (8g, 85.9mmol), TEA (9.47g, 93.7mmol) in toluene was added a solution of 9 (10g, 42.7mmol) in toluene dropwise. The reaction was continued 2-3hat room temperature, then partial solvent was distilled off and filtered with the filter cake being washed by water and small amount of toluene to obtain 11a, awhite solid (9 g, 72% yield).
65%	In toluene; at 20℃;	The raw material benzylamine (4b, 4.2g, 40mmol) and 100mL of toluene were placed in a 500mL round bottom flask at room temperature.Dissolve Intermediate 3 in 100 mL of toluene.Filtration, the filtrate was dropped into the reaction flask under stirring, and the reaction was continued at room temperature for 2-3 hours.After the TLC detection reaction is completed, part of the solvent is distilled off, filtered, and the filter cake is rinsed with water and a small amount of toluene, respectively.Obtained 4.2 g of a white solid in 65% yield.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 282 - 291
[2]Patent: CN108299255,2018,A .Location in patent: Paragraph 0045; 0051; 0052
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5364 - 5368

51
[ 63555-50-0 ]
[ 1254205-89-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5364 - 5368
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5364 - 5368

52
[ 63555-50-0 ]
[ 1254207-52-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5364 - 5368
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5364 - 5368

53
N-(3-methoxyphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
methyl 3-[({3-[(3-methoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

54
N-(3-methoxyphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
3-[({3-[(3-methoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

55
N-(2,5-dimethoxyphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
methyl 3-[({3-[(2,5-dimethoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

56
N-(2,5-dimethoxyphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
3-[({3-[(2,5-dimethoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

57
N-(5-methoxy-2-methylphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
methyl 3-[({3-[(5-methoxy-2-methylphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

58
N-(5-methoxy-2-methylphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
3-[({3-[(5-methoxy-2-methylphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

59
N-(2-chloro-5-methoxyphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
methyl 3-[({3-[(2-chloro-5-methoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

60
N-(2-chloro-5-methoxyphenyl)pyrazin-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
3-[({3-[(2-chloro-5-methoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

61
N<SUP>2</SUP>-(3,5-dimethoxyphenyl)pyrazine-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
methyl 3-[({3-[(3,5-dimethoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

62
N<SUP>2</SUP>-(3,5-dimethoxyphenyl)pyrazine-2,3-diamine [ No CAS ]
[ 63555-50-0 ]
3-[({3-[(3,5-dimethoxyphenyl)amino]pyrazin-2-yl}amino)sulfonyl]benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 212 - 221

63
5'-bromo-2'-cyclopropyl-1',2'-dihydrospiro[cyclohexane-1,3'-indole] [ No CAS ]
[ 63555-50-0 ]
methyl 3-[(5'-bromo-2'-cyclopropylspiro[cyclohexane-1,3'-indol]-1'(2'H)-yl)sulfonyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine; at 20℃; for 17h;	A mixture of indoline B.3 (2.80 g, 9.14 mmol), methyl 3-(chlorosulfonyl)benzoate (CAS No. [63555-50-0]; 3.22 g, 13.7 mmol) and pyridine (7.4 ml, 91 mmol) was stirred at rt for 17 h. The reaction mixture was partitioned between aqueous saturated sodium hydrogencarbonate solution and dichloromethane and extracted with dichloromethane. The combined organic layers were washed with brine, dried with sodium sulfate and concentrated in vacuo. The obtained crude material was purified by flash chromatography (SiO2[KP-NH]-hexane/ethyl acetate) to give the title compound (3.1 g, 67%). 1H-NMR (400MHz, CDCl3): Shift [ppm]= 0.14 - 0.17 (m, 1H), 0.40 - 0.47 (m, 1 H), 0.51 - 0.57 (m, 1 H), 0.63 - 0.76 (m, 3H), 0.95 - 1.03 (m, 1 H), 1.14 - 1.29 (m, 3H), 1.41 - 1.52 (m, 1 H), 1.64 - 1.71 (m, 2H), 1.76 - 1.81 (m, 1 H), 2.11 - 2.14 (m, 1 H), 3.94 - 3.96 (m, 4H), 7.13 (d, 1 H), 7.32 (dd, 1 H), 7.47 - 7.52 (m, 2H), 7.90 (dd, 1 H), 8.19 (dd, 1 H), 8.46 - 8.47 (m, 1 H)

Reference： [1]Patent: EP2881391,2015,A1 .Location in patent: Paragraph 0141; 0142

64
1,4-diaminonaphthalene dihydrochloride [ No CAS ]
[ 63555-50-0 ]
C₂₆H₂₂N₂O₈S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With pyridine; at 20℃; for 24h;	General procedure: These previously unreported compounds were synthesized accordingto a known, similar procedure [48]. A solution of 1,4-diaminonaphthalene dihydrochloride (1 equivalent) andsubstituted-benzenesulfonyl chloride (2.2 equivalent) in pyridine(3-5 mL) was allowed stir at room temperature for 24 h. Oncompletion, the reaction mixture was diluted with EtOAc (40 mL),washed with H2O (2 50 mL) and HCl (2 N, 2 50 mL), dried (Na2SO4) and evaporated to yield crude products, which were recrystallized or washed with appropriate solvents to yield purecompounds. 2.9.1.4 Synthesis of 3,3'-(((4-(hydrosulfonylamino)naphthalen-1-yl)amino)sulfonyl)dibenzoic acid (11d) The crude methyl ester was washed with Et2O to afford 0.21 g (58% yield) of the methyl ester of 11d as a purple solid. 1H NMR (400 MHz, DMSO-d6, delta): 10.41 (s, 2H), 8.28 (s, 2H), 8.13 (d, J = 8.0 Hz, 2H), 7.89 (dd, J = 6.4, 3.2 Hz, 2H), 7.80 (d, J = 8.0 Hz, 2H), 7.61 (t, 2H), 7.37 (dd, J = 6.4, 3.0 Hz, 2H), 6.98 (s, 2H), 3.85 (s, 6H).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 252 - 268

65
1,4-diaminonaphthalene dihydrochloride [ No CAS ]
[ 63555-50-0 ]
C₂₄H₁₈N₂O₈S₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 252 - 268

66
[ 533-58-4 ]
[ 63555-50-0 ]
methyl 3-[(2-iodophenyl)oxysulfonyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With pyridine; dmap; at 20℃; for 72h;	General procedure: Typically to a stirred solution of the arylsulfonyl chloride (2.7 mmol) and 4-DMAP (28mg, 0.23 mmol) in pyridine (20 mL) at room temperature was added 2-iodophenol (0.50g, 2.3 mmol), and the reaction mixture stirred for 3 days at room temperature. The reaction mixture was concentrated, dissolved in toluene (ca. 10 mL) and the resulting solution evaporated in vacuo to azeotropically remove the pyridine. The residue was partitioned between CH2Cl2 and water, the organic layer separated, and the aqueous phase re-extracted twice with more CH2Cl2. The combined organic extract was washed with brine, dried over MgSO4 and evaporated in vacuo. Purification of the residue by column chromatography on silica gel furnished the corresponding sulfonate.

Reference： [1]Tetrahedron,2015,vol. 71,p. 6701 - 6719

67
[ 63555-50-0 ]
methyl 3-(2-methylaminophenyl)benzoate [ No CAS ]
methyl 6-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide-3-carboxylate [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 6701 - 6719

68
[ 63555-50-0 ]
methyl (4aRS,10bRS)-4a,10b-dihydrodibenzo[c,e][1,2]oxathiine-6,6-dioxide-8-carboxylate [ No CAS ]
methyl dibenzo[c,e][1,2]oxathiine-6,6-dioxide-8-carboxylate [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 6701 - 6719

69
[ 63555-50-0 ]
methyl 3-[[(2-iodophenyl)methylamino]sulfonyl]benzoate [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 6701 - 6719

70
[ 615-43-0 ]
[ 63555-50-0 ]
methyl 3-[[(2-iodophenyl)amino]sulfonyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With pyridine; dmap; at 20℃; for 48h;	General procedure: Typically a mixture of 2-iodoaniline (1.1 g, 5.0 mmol), 4-DMAP (30 mg, 0.24 mmol) and the arylsulfonyl chloride (6.0 mmol) in pyridine (10 mL) was stirred at room temperature for 2 days. The pyridine was removed in vacuo, the residue dissolved in CH2Cl2 (25 mL) washed with saturated aqueous CuSO4 (2x20 mL) and water (20 mL), dried over MgSO4, filtered, the solvent removed in vacuo and the residue purified by column chromatography or crystallisation.

Reference： [1]Tetrahedron,2015,vol. 71,p. 6701 - 6719

71
6-amino-1-ethylbenzo[cd]indol-2(1H)-one [ No CAS ]
[ 63555-50-0 ]
methyl 3-(N-(1-ethyl-2-oxo-1,2-dihydrobenzo[cd]indol-6-yl)sulfamoyl)benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 1565 - 1579

72
[ 63555-50-0 ]
3-[cycloheptyl(methyl)sulfamoyl]benzoic acid [ No CAS ]