[ CAS No. 53297-70-4 ] {[proInfo.proName]}

Name: 53297-70-4|4-Amino-3-methylbenzenesulfonamide|97%
Brand: Ambeed
SKU: A108465
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Quality Control of [ 53297-70-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53297-70-4 ]

Product Details of [ 53297-70-4 ]

CAS No. :	53297-70-4	MDL No. :	MFCD00466840
Formula :	C₇H₁₀N₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IGQGXIVCGKMRAM-UHFFFAOYSA-N
M.W :	186.23	Pubchem ID :	143037
Synonyms :

Calculated chemistry of [ 53297-70-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.81
TPSA :	94.56 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.06
Log Po/w (XLOGP3) :	-0.18
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	0.05
Log Po/w (SILICOS-IT) :	-0.3
Consensus Log Po/w :	0.39

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.19
Solubility :	12.2 mg/ml ; 0.0653 mol/l
Class :	Very soluble
Log S (Ali) :	-1.35
Solubility :	8.32 mg/ml ; 0.0447 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.99
Solubility :	1.89 mg/ml ; 0.0102 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 53297-70-4 ]

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

Application In Synthesis of [ 53297-70-4 ]

* 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 [ 53297-70-4 ]
Downstream synthetic route of [ 53297-70-4 ]

[ 53297-70-4 ] Synthesis Path-Upstream 1~3

1
[ 252562-03-1 ]
[ 53297-70-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride In ethanol; water at 80℃;	A mixture of N-(2-methyl-4-sulfamoylphenyl)acetamide (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na2CO3 (aq) to pH = 8. The mixture was extracted with EA (80 mL x 4), dried over Na2SO4, and concentrated to obtain 4-amino-3-methylbenzenesulfonamide as a pale solid (4.9 g, yield 100percent).
100%	With hydrogenchloride; water In ethanolReflux	Compound 27-6 (0455) A mixture of 27-5 (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na₂CO₃(aq) to PH=8. The mixture was extracted with EA (80 ml×4), dried over Na₂SO₄, and concentrated to give 27-6 as a pale solid (4.9 g, yield 100percent).
93%	Stage #1: With hydrogenchloride In ethanol; waterHeating / reflux Stage #2: With sodium hydrogencarbonate In ethanol; water at 20℃;	A round-bottom flask was equipped with a stir bar, a reflux condenser and nitrogen on demand. Into the flask were placed sulfonamide 465 (8.4 g, 36.80 mmol), ethyl alcohol (200 mL) and 2N hydrochloric acid (128 mL). The resulting mixture was allowed to heat to reflux overnight, after which time it was allowed to cool to RT and was neutralized with saturated, aqueous sodium bicarbonate. It was then poured into a separatory funnel containing water and ethyl acetate, the organic layer was collected, washed with water, brine, dried over MgSO₄, filtered and the solvents were removed under reduced pressure to afford a tan solid (6.35 g, 93percent), which was used without further purification. ¹H NMR (DMSO-d₆, 400 MHz) δ 2.06 (s, 3H), 5.54 (s, 2H), 6.58 (d, J= 12 Hz, 1H), 6.82 (s, 2H), 7.30 (d, J= 12 Hz, 1H), 7.33 (s, 1H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2338 - 2342
[2] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 304
[3] Patent: EP1208091, 2006, B1, . Location in patent: Page/Page column 8; 21
[4] Collection of Czechoslovak Chemical Communications, 1948, vol. 13, p. 161,165,169
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 5, p. 1175 - 1182

2
[ 14988-21-7 ]
[ 53297-70-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 5, p. 1175 - 1182
[2] Patent: US9138427, 2015, B2,

3
[ 98-33-9 ]
[ 53297-70-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2338 - 2342
[2] Patent: US9138427, 2015, B2,

[ 53297-70-4 ] Synthesis Path-Downstream 1~71

1
[ 112-77-6 ]
[ 53297-70-4 ]
6-oleoylamino-toluenesulfonamide-⁽³⁾ [ No CAS ]

Reference： [1]Patent: US2169971,1937,

2
[ 252562-03-1 ]
[ 53297-70-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In ethanol; water; at 80℃;	A mixture of N-(2-methyl-4-sulfamoylphenyl)acetamide (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na2CO3 (aq) to pH = 8. The mixture was extracted with EA (80 mL x 4), dried over Na2SO4, and concentrated to obtain 4-amino-3-methylbenzenesulfonamide as a pale solid (4.9 g, yield 100%).
100%	With hydrogenchloride; water; In ethanol;Reflux;	Compound 27-6 (0455) A mixture of 27-5 (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na2CO3(aq) to PH=8. The mixture was extracted with EA (80 ml×4), dried over Na2SO4, and concentrated to give 27-6 as a pale solid (4.9 g, yield 100%).
93%		A round-bottom flask was equipped with a stir bar, a reflux condenser and nitrogen on demand. Into the flask were placed sulfonamide 465 (8.4 g, 36.80 mmol), ethyl alcohol (200 mL) and 2N hydrochloric acid (128 mL). The resulting mixture was allowed to heat to reflux overnight, after which time it was allowed to cool to RT and was neutralized with saturated, aqueous sodium bicarbonate. It was then poured into a separatory funnel containing water and ethyl acetate, the organic layer was collected, washed with water, brine, dried over MgSO4, filtered and the solvents were removed under reduced pressure to afford a tan solid (6.35 g, 93%), which was used without further purification. 1H NMR (DMSO-d6, 400 MHz) delta 2.06 (s, 3H), 5.54 (s, 2H), 6.58 (d, J= 12 Hz, 1H), 6.82 (s, 2H), 7.30 (d, J= 12 Hz, 1H), 7.33 (s, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2338 - 2342
[2]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 304
[3]Patent: EP1208091,2006,B1 .Location in patent: Page/Page column 8; 21
[4]Collection of Czechoslovak Chemical Communications,1948,vol. 13,p. 161,165,169
[5]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182

3
[ 53297-70-4 ]
[ 111-92-2 ]
[ 75-36-5 ]
2-Methyl-benzene-1,4-disulfonic acid 4-(acetyl-amide) 1-dibutylamide [ No CAS ]

Reference： [1]Patent: DE2047384,1971,
Chem.Abstr.,1971,vol. 75

4
[ 53297-70-4 ]
[ 329944-30-1 ]
2-[4-chloro-2-(3-cyano-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182

5
[ 53297-70-4 ]
[ 675139-67-0 ]
GW₄₅₁₁ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182

6
[ 436095-23-7 ]
[ 53297-70-4 ]
N-[4-(aminosulfonyl)-2-methylphenyl]-2-[(1-mesityl-1H-tetrazol-5-yl)thio]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; In chloroform; toluene; at 20 - 70℃; for 4.5h;	The compounds in Table 2 below were prepared in accordance with the procedures set forth in Example 1, Step 3 using either [(1-mesityl-1H-tetrazol-5-yl)thio]acetic acid (prepared as described in Example 1, Steps 2 and 3) or the appropriate counterpart and the appropriate amine in place of 2-chloro-3-aminopyridine.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2748 - 2752
[2]Patent: WO2005/115147,2005,A2 .Location in patent: Page/Page column 35-36

7
[ 329943-23-9 ]
[ 53297-70-4 ]
2-[2-(3-cyano-benzoyl)-4-trifluoromethyl-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

8
[ 53297-70-4 ]
[ 598-21-0 ]
[ 329944-57-2 ]

Yield	Reaction Conditions	Operation in experiment
69%	With pyridine; In chloroform; at 0 - 20℃; for 18.3333h;	A solution of 466 (5.0 g, 26.85 mol) and pyridine (2.4 mL, 29.53 mmol) in 150 mL of chloroform was cooled to 0 C in an ice bath. Bromoacetyl bromide (2.6 mL, 29.53 mmol) was added dropwise over 20 min, and the resulting mixture was allowed to slowly warm to room temperature as it was stirred for 18 h. The reaction mixture was then poured into 150 mL of water and extracted with two 100-mL portions of CH2Cl2. Both the organic and aqueous layers were filtered to yield a beige solid. This solid was suspended in 40 mL of 1 N HCl and stirred several minutes. The solid was then filtered and rinsed with CH2Cl2, MeOH, and hexanes to yield 470 (5.705 g, 69%): 1H NMR (CDCl3, 400 MHz) delta 9.84 (s, 1H), 7.66-7.56 (m, 3 H), 7.23 (br s, 2 H), 4.09 (s, 2 H), 2.24 (s, 3 H).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739
[2]Patent: EP1208091,2006,B1 .Location in patent: Page/Page column 22-23

9
[ 53297-70-4 ]
[ 329944-70-9 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

10
[ 53297-70-4 ]
2-[2-(3,5-difluoro-benzoyl)-thiophen-3-yloxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

11
[ 53297-70-4 ]
2-[4-chloro-2-(3-chloro-5-methyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

12
[ 53297-70-4 ]
2-[4-chloro-2-(3,5-dimethyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

13
[ 53297-70-4 ]
2-[4-chloro-2-(5-cyano-pyridine-3-carbonyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

14
[ 53297-70-4 ]
2-[4-chloro-2-(3,5-dimethoxy-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

15
[ 53297-70-4 ]
2-[2-(3-bromo-5-chloro-benzoyl)-4-chloro-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

16
[ 53297-70-4 ]
2-[4-chloro-2-(3-cyano-5-methyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

17
[ 53297-70-4 ]
2-[2-(3-bromo-5-trifluoromethyl-benzoyl)-4-chloro-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

18
[ 53297-70-4 ]
2-[4-chloro-2-(3-cyano-5-trifluoromethyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

19
[ 53297-70-4 ]
N-[4-(aminosulfonyl)-2-methylphenyl]-2-[4-chloro-2-(3-chloro-5-cyanobenzoyl)phenoxy]acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 727 - 739

20
[ 14988-21-7 ]
[ 53297-70-4 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182
[2]Patent: US9138427,2015,B2

21
sodium 4-(acetylamino)-3-methylbenzenesulfonate [ No CAS ]
[ 53297-70-4 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182
[2]Patent: US9138427,2015,B2

22
[ 1007571-96-1 ]
[ 53297-70-4 ]
2-[4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		A 100 mL round bottom was charged with <strong>[53297-70-4]4-amino-3-methyl-benzenesulfonamide</strong> (0.260 g, 1.40 mmol) and dissolved in 5 mL of acetone and NaHCO3 (0.117 g, 1.40 mmol) under nitrogen. To the stirred mixture was added dropwise 162b (0.500 g, 1.40 mmol) dissolved in 7 mL of acetone and resulting mixture stirred for 24 h at RT. When starting material was consumed the reaction mixture was cooled to 0 C. and quenched with 10% aqueous HCl. The reaction mixture was extracted with EtOAc and washed with aqueous 10% HCl, water, and brine. The organic extracts were dried (Na2SO4) and filtered. The solvent was removed in vacuo to yield a crude solid which was purified by SiO2 chromatography eluting with DCM/MeOH (93:7) to afford 0.64 g (90%) of I-42: ms (M-H)=507; mp: 250.1-252.3 C.; Elemental Analysis: calcd; C, 51.98; H, 3.17; N, 8.27, found: C, 51.20; H, 3.01; N, 8.10 (with 0.4M H2O).

Reference： [1]Patent: US2005/239881,2005,A1 .Location in patent: Page/Page column 41-42

23
[ 1056598-54-9 ]
[ 53297-70-4 ]
2-[4-Bromo-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		A 100 if L round bottom flask was charged with <strong>[53297-70-4]4-amino-3-methyl-benzenesulfonamide</strong> (0.092 g, 0.495 mmol), dissolved in 2 mL of acetone and NaHCO3 (0.040 g, 0.495 mmol) was added. To the stirred suspension under a nitrogen atmosphere was added dropwise a solution of the acid chloride from step 4 (0.200 g, 0.495 mmol) dissolved in 3 mL acetone and the reaction was stirred for 24 h at RT. The reaction mixture was cooled to 0 C. and quenched with 10% aqueous HCl. The aqueous phase was extracted with EtOAc and the combined extracts were washed with aqueous 10% HCl, water, and brine. The organic phase was dried(Na2SO4), filtered and the solvent was removed in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (93:7) to afford 0.240 g (87%) of I-189: ms (M-H)=551, mp 244.0-245.1; Anal. CHN; calcd C, 47.80; H, 2.92; N, 7.60; found C, 47.51; H, 2.80; N, 7.49.
87%		A 100 if L round bottom flask was charged with <strong>[53297-70-4]4-amino-3-methyl-benzenesulfonamide</strong> (0.092 g, 0.495 mmol), dissolved in 2 mL of acetone and NaHCO3 (0.040 g, 0.495 mmol) was added. To the stirred suspension under a nitrogen atmosphere was added dropwise a solution of the acid chloride from step 4 (0.200 g, 0.495 mmol) dissolved in 3 mL acetone and the reaction was stirred for 24 h at RT. The reaction mixture was cooled to 0 C. and quenched with 10% aqueous HCl. The aqueous phase was extracted with EtOAc and the combined extracts were washed with aqueous 10% HCl, water, and brine. The organic phase was dried(Na2SO4), filtered and the solvent was removed in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (93:7) to afford 0.240 g (87%) of I-189: ms (M-H)=551, mp 244.0-245.1; Anal. CHN; calcd C, 47.80; H, 2.92; N, 7.60; found C, 47.51; H, 2.80; N, 7.49.

Reference： [1]Patent: US2005/239881,2005,A1 .Location in patent: Page/Page column 48
[2]Patent: US2005/239881,2005,A1 .Location in patent: Page/Page column 48

24
C₁₀H₁₅N₃O₂S [ No CAS ]
[ 53297-70-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of 2-aminotoluene-5-sulfonic acid (1.0 wt, 1.0 eq. 6.41 mol) in dichloromethane (15 vol) and N,N-dimethylformamid (0.43 wt, 1.1 equiv.,) was added oxalyl chloride (1.53 wt, 2.25 equiv.) over a period of 120 minutes. Additional dichloromethane (1 volume) was added and the resulting mixture stirred at ambient temp 3 hours. IPC of methanol-quenched aliquot (TLC, 8% MeOH-DCM and HPLC normal phase fast LC) showed complete conversion to activated, protected intermediate. Methylene chloride was removed under gentle reflux at atmospheric pressure to approximately 5 volumes and replaced with dimethoxyethane (7.5 vol). The mixture was evaporated under vacuum with a jacket temperature of 65 degrees to approximately 5 volumes and diluted with additional DME (2.5 volumes). The resulting mixture was cooled to 15 degrees and treated with a solution of 28% ammonium hydroxide (2.23 vol., 3 equiv.) added over a period of 15 minutes which results in momentary dissolution of the intermediate followed quickly by precipitation of the protected intermediate. IPC (TLC, normal phase fast LC) showed complete conversion to protected sulphonamide. The intermediate was filtered, and the solid washed with water (2×1 vol), and then placed back in the reactor. The reactor was charged with a solution of LiOH (0.45 wt., 2 equiv) in 9:1 water:methanol (8 vol based on original input). The resulting solution was warmed to 50 degrees for 5 hours or until IPC (TLC and normal phase fast LC) showed complete hydrolysis to a compound of formula (V). Decolorizing carbon (1.0 weight %) and celite (5.0 weight %) was added and the mixture stirred briefly and filtered through filter cloth into reactor B. The solution was cooled to 25 degrees and adjusted to pH 9 with addition 6 N hydrochloric acid (approximately 1.6 vol.) over a period of 15 minutes with vigorous stirring. The solution was maintained at 45 to 55 degrees for a 2 to 4 hour period to allow conversion from the original amorphous precipitate to a crystalline solid, then cooled to 20 degrees and filtered. The resulting crystalline solid was washed with 90% water/methanol (1 volume) followed by water (2×1 volumes) and dried in vacuum oven at 50 degrees with nitrogen sweep for 16 hours.

Reference： [1]Patent: US2006/183944,2006,A1 .Location in patent: Page/Page column 4

25
[ 53297-70-4 ]
[ 79-04-9 ]
[ 53297-88-4 ]

Yield	Reaction Conditions	Operation in experiment
		a. 2-Chloro-N-(2-methyl-4-sulphamoylphenyl)-acetamide <strong>[53297-70-4]2-methyl-4-sulphamoylaniline</strong> (18,6 g) and alpha-chloroacetyl chloride (30g) were refluxed together 30 min. and the mixture worked up as in Example 2(a) to yield 11 g, m.p. 193-194 C9 H11 ClN2 O3 S (262,7) Requires: C: 41,14 H: 4,22 N: 10,66%. Found: C: 41,23 H: 4,30 N: 10,65%.

Reference： [1]Patent: US3963706,1976,A

26
[ 263270-52-6 ]
[ 53297-70-4 ]
[ 1114592-11-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 0℃; for 0.5h;	A cooled (0 0C) solution of e-chloropyhmidine^-carbonyl chloride (4.56 g; 25.8 mmol) in DCM (80 ml) was treated dropwise over 30 minutes with a solution of <strong>[53297-70-4]4-amino-3-methyl-benzenesulfonamide</strong> (4.00 g; 21.5 mmol) and DIEA (7.40 ml; 43.0 mmol) in anhydrous DMF (10 ml_). At the end of addition the reaction mixture was concentrated under vacuum and the residue was taken up in EtOAc (200 mL). The organic phase was washed with water/brine (80 mL). A precipitate was formed, which was filtered and dried under vacuum to afford the crude product which was recrystallized from EtOH. The title product was obtained as a white solid. 1H NMR (300MHz, DMSO-d6) delta 10.65 (1 H, br s), 9.31 (1 H, d, J= 1.1 Hz), 8.24 (1 H, d, J= 1.1 Hz), 7.85-7.68 (3H, m), 7.33 (2H, br s), 2.36 (3H, s). MS (ESI-): 325.1. HPLC (Condition A): Rt 2.73 min (HPLC purity 100.0%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1516 - 1519
[2]Patent: WO2009/19167,2009,A1 .Location in patent: Page/Page column 110

27
[ 1124329-94-7 ]
[ 53297-70-4 ]
[ 1124329-10-7 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of <strong>[53297-70-4]4-amino-3-methylbenzenesulfonamide</strong> (0.075 g), 4-methylbenzene-sulfonic acid (0.1 g) and 2-chloro-9-cyclopentyl-7-methyl-purin-8-one (Method 4, 0.075 g) in 4-methyl-2-pentanol (1.5 mL) was heated at 2000C for 5 mins by microwave then cooled to r.t. The reaction was repeated on an identical scale but using 1-butanol (1.5 mL) in place of 4-methyl-2-pentanol. The combined reaction mixtures were purified by SCX, eluting with 2M NH3 in MeOH to give a coloured gum. The gum was purified by reverse phase basic HPLC to afford the title compound (0.05 g, 21%) as a colourless solid; 1H NMR: (CDCl3) 1.69-1.75 (2H, m), 1.96-2.05 (4H, m), 2.26-2.31 (2H, m), 2.40 (3H, s), 3.41 (3H, s), 4.70 (2H, s), 4.79-4.88 (IH, m), 6.98 (IH, d), 7.75 (IH, d), 7.77-7.79 (IH, m), 7.90 (IH, s), 8.54 (IH, d); m/r. MH+ 403; EAA: 1.28; EAA2: 0.0166.
		A mixture of <strong>[53297-70-4]4-amino-3-methylbenzenesulfonamide</strong> (0.075 g), 4-methylbenzene-sulfonic acid (0.1 g) and 2-chloro-9-cyclopentyl-7-methyl-purin-8-one (Method 4, 0.075 g) in 4-methyl-2-pentanol (1.5 mL) was heated at 2000C for 5 mins by microwave then cooled to r.t. The reaction was repeated on an identical scale but using 1-butanol (1.5 mL) in place of 4-methyl-2-pentanol. The combined reaction mixtures were purified by SCX, eluting with 2M NH3 in MeOH to give a coloured gum. The gum was purified by reverse phase basic HPLC to afford the title compound (0.05 g, 21%) as a colourless solid; 1H NMR: (CDCl3) 1.69-1.75 (2H, m), 1.96-2.05 (4H, m), 2.26-2.31 (2H, m), 2.40 (3H, s), 3.41 (3H, s), 4.70 (2H, s), 4.79-4.88 (IH, m), 6.98 (IH, d), 7.75 (IH, d), 7.77-7.79 (IH, m), 7.90 (IH, s), 8.54 (IH, d); m/r. MH+ 403; EAA: 1.28; EAA2: 0.0166.

Reference： [1]Patent: WO2009/24824,2009,A1 .Location in patent: Page/Page column 66
[2]Patent: WO2009/24824,2009,A1 .Location in patent: Page/Page column 66

28
[ 952504-50-6 ]
[ 53297-70-4 ]
[ 1296198-11-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of Intermediate 1 (0.10 g, 0.381 mmol) in CH2CI2 (5.0 mL) was added diisopropyl ethyl amine (0.1 mL, 0.572 mmol) and a 50% solution of propyiphosphonic anhydride in ethyl acetate (0.340 mL, 0.572 mmol). The mixture was stirred for 30 minutes at room temperature. 4-Amino-3- methylbenzenesulfonamide [CAS No. 53297-70-4] (0.071 g, 0.381 mmol) was added to the reaction mixture at room temperature and stirred overnight. The reaction mixture was then poured onto ice water (25 mL) and CH2CI2 (25 mL) added. The organic layer was separated and washed with brine (25 mL), dried with Na2SO4, filtered and concentrated to dryness. The residue was triturated with Ch C^/Hexanes and then the solid was purified with a MPLC to give the title compound as a white solid.1H NMR (300 MHz, DMSO-d6) delta 10.95 (s, 1 H), 9.03 (s, 1 H), 8.46 (d, J = 8.5 Hz, 1 H), 7.97 (d, J = 9.1 Hz, 1 H), 7.79-7.65 (m, 2H), 7.33-7.18 (m, 3H), 3.98 (s, 3H), 2.81 -2.71 (m, 2H), 2.43 (s, 3H), 1 .64-1 .50 (m, 2H), 0.94 (t, J = 7.4 Hz, 3H).

Reference： [1]Patent: WO2011/50054,2011,A2 .Location in patent: Page/Page column 53

29
[ 1338799-46-4 ]
[ 53297-70-4 ]
[ 1208317-17-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	In acetic acid; at 120℃;	A mixture of 3-(2-(3-(5-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-3-oxopropyl)-1,3-dioxolan-2-yl)propanoic acid (200 mg, 0.549 mmol) and <strong>[53297-70-4]4-amino-3-methylbenzenesulfonamide</strong> (123 mg, 0.659 mmol) in 3 mL of AcOH was heated at 120 C overnight , then the solvent was removed under reduced pressure and the residue was purified by Pre-HPLC. The product was obtained (80 mg, yield 31%) with purity 99.33% (254 nm) and 99.47% (214 nm).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2338 - 2342

30
[ 98-33-9 ]
[ 53297-70-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2338 - 2342
[2]Patent: US9138427,2015,B2

31
4-acetamido-3-methylbenzenesulfonic acid [ No CAS ]
[ 53297-70-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2338 - 2342
[2]Patent: US9138427,2015,B2

32
[ 53297-70-4 ]
[ 1341199-24-3 ]