[ CAS No. 138-39-6 ] {[proInfo.proName]}

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Quality Control of [ 138-39-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 138-39-6 ]

CAS No. :	138-39-6	MDL No. :	MFCD00072084
Formula :	C₇H₁₀N₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TYMRLRRVMHJFTF-UHFFFAOYSA-N
M.W :	186.23	Pubchem ID :	3998
Synonyms :	NSC 34632

Safety of [ 138-39-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 138-39-6 ]

* 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 [ 138-39-6 ]
Downstream synthetic route of [ 138-39-6 ]

[ 138-39-6 ] Synthesis Path-Upstream 1~10

1
[ 864528-35-8 ]
[ 138-39-6 ]

Reference： [1] Patent: WO2014/144871, 2014, A1, . Location in patent: Page/Page column 144
[2] Patent: WO2015/95953, 2015, A1, . Location in patent: Page/Page column 122

2
[ 3119-02-6 ]
[ 138-39-6 ]

Reference： [1] Helvetica Chimica Acta, 2006, vol. 89, # 6, p. 1254 - 1257
[2] Yakugaku Zasshi, 1949, vol. 69, p. 417[3] Chem.Abstr., 1950, p. 1924
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 2099,2101

3
[ 2015-14-7 ]
[ 138-39-6 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 1459
[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1948, vol. 21, p. 681,683[3] Chem.Abstr., 1952, p. 5540
[4] DRP/DRBP Org.Chem.,
[5] DRP/DRBP Org.Chem.,
[6] Patent: US2288531, 1940, ,

4
[ 28073-51-0 ]
[ 138-39-6 ]

Reference： [1] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1948, vol. 21, p. 681,683[2] Chem.Abstr., 1952, p. 5540
[3] DRP/DRBP Org.Chem.,
[4] Journal of the American Chemical Society, 1944, vol. 66, p. 1459
[5] DRP/DRBP Org.Chem.,
[6] Patent: US2288531, 1940, ,

5
[ 14289-29-3 ]
[ 138-39-6 ]

Reference： [1] Journal of the American Chemical Society, 1940, vol. 62, p. 2099,2101

6
[ 588-46-5 ]
[ 138-39-6 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 1459

7
[ 40724-47-8 ]
[ 138-39-6 ]

Reference： [1] Patent: WO2014/144871, 2014, A1,

8
[ 2522-79-4 ]
[ 138-39-6 ]

Reference： [1] DRP/DRBP Org.Chem.,

9
[ 7664-41-7 ]
[ 102153-43-5 ]
[ 138-39-6 ]

Reference： [1] Kogyo Kagaku Zasshi, 1949, vol. 52, p. 114,117, 118[2] Chem.Abstr., 1951, p. 2149

10
[ 2389-73-3 ]
[ 7664-41-7 ]
[ 138-39-6 ]

Reference： [1] Kogyo Kagaku Zasshi, 1949, vol. 52, p. 114,117, 118[2] Chem.Abstr., 1951, p. 2149

[ 138-39-6 ] Synthesis Path-Downstream 1~37

1
[ 3119-02-6 ]
[ 138-39-6 ]

Yield	Reaction Conditions	Operation in experiment
82.2%	With ammonium hydroxide; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 0.5h;Inert atmosphere;	<strong>[3119-02-6]4-cyanobenzenesulfamide</strong> (500 mg, 2.74 mmol), methanol (3 mL), tetrahydrofuran (1 mL), aqueous ammonia (0.5 mL) and Raney Ni (100 mg) were added to a 20 mL single-mouth bottle, and the mixture reacted at room temperature for 30 min under the hydrogen atmosphere, filtered and concentrated in vacuo to give the product of 4-(aminomethyl)benzenesulfonamide (white solid, 420 mg), with a yield of 82.2%. 1H NMR (400 MHz, DMSO) delta 7.74 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 7.9 Hz, 2H), 7.29 (s, 2H), 3.77 (s, 2H). MS (ESI m/z: 187.0 (M-1).

Reference： [1]Helvetica Chimica Acta,2006,vol. 89,p. 1254 - 1257
[2]Patent: EP3476829,2019,A1 .Location in patent: Paragraph 0071
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1949,vol. 69,p. 417
Chem.Abstr.,1950,p. 1924
[4]Journal of the American Chemical Society,1940,vol. 62,p. 2099,2101

2
[ 138-39-6 ]
[ 877-89-4 ]
4-[(4,6-dimethoxy-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate

Reference： [1]Bretschneider; Kloetzer [Monatshefte fur Chemie, 1956, vol. 87, p. 120,126]

3
[ 138-39-6 ]
[ 2566-19-0 ]
[ 814-68-6 ]
N-([(4-Sulfamoyl-benzylcarbamoyl)-methyl]-carbamoyl}-methyl)-acrylamide [ No CAS ]

Reference： [1]Analytical Chemistry,1993,vol. 65,p. 1314 - 1322

4
[ 138-39-6 ]
[ 2736-23-4 ]
[ 23823-12-3 ]

Reference： [1]Farmaco, Edizione Scientifica,1969,vol. 24,p. 199 - 220

5
[ 138-39-6 ]
[ 97-08-5 ]
4-Chloro-3-nitro-N-(4-sulfamoyl-benzyl)-benzenesulfonamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 463 - 474

6
[ 873-58-5 ]
[ 138-39-6 ]
[ 729-46-4 ]
C₁₂H₁₇N₃O₃S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sodium hypochlorite at 25 - 30℃;

Reference： [1]Scozzafava, Andrea; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 10, p. 1117 - 1120]

7
[ 138-39-6 ]
[ 16629-19-9 ]
[ 1955-46-0 ]
N-(4-sulfamoyl-benzyl)-5-(thiophene-2-sulfonylamino)-isophthalamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1998,vol. 8,p. 187 - 205

8
[ 138-39-6 ]
[ 1955-46-0 ]
[ 494-19-9 ]
[ 32315-10-9 ]
5-[(10,11-dihydro-dibenzo[b,f]azepine-5-carbonyl)-amino]-N-(4-sulfamoyl-benzyl)-isophthalamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1998,vol. 8,p. 187 - 205

9
[ 138-39-6 ]
[ 1205-30-7 ]
4-chloro-3-sulfamoyl-N-(4-sulfamoyl-benzyl)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 16h;

Reference： [1]Mincione, Francesco; Starnotti, Michele; Menabuoni, Luca; Scozzafava, Andrea; Casini, Angela; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 13, p. 1787 - 1791]

10
[ 138-39-6 ]
[ 23911-25-3 ]
{(2-{carboxymethyl-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-ethyl)-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1466 - 1476

11
[ 138-39-6 ]
[ 139-13-9 ]
{carboxymethyl-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-homosulfanilamide; nitrilotriacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetone at 20℃; for 0.25h; Stage #2: With triethylamine In acetone at 4℃; Further stages.;

Reference： [1]Scozzafava, Andrea; Menabuoni, Luca; Mincione, Francesco; Supuran, Claudiu T. [Journal of Medicinal Chemistry, 2002, vol. 45, # 7, p. 1466 - 1476]

12
[ 138-39-6 ]
[ 67-42-5 ]
{(2-{2-[2-(bis-carboxymethyl-amino)-ethoxy]-ethoxy}-ethyl)-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1466 - 1476

13
[ 138-39-6 ]
[ 81-23-2 ]
(R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 4-sulfamoyl-benzylamide [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1551 - 1557

14
[ 138-39-6 ]
[ 776-09-0 ]
2,3,5,6-Tetrafluoro-N-(4-sulfamoyl-benzyl)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In N,N-dimethyl acetamide for 1h; cooling;
	With sodium hydroxide at 20℃;

Reference： [1]De Leval, Xavier; Ilies, Monica; Casini, Angela; Dogné, Jean-Michel; Scozzafava, Andrea; Masini, Emanuela; Mincione, Francesco; Starnotti, Michele; Supuran, Claudiu T. [Journal of Medicinal Chemistry, 2004, vol. 47, # 11, p. 2796 - 2804]
[2]Vullo, Daniela; Scozzafava, Andrea; Pastorekova, Silvia; Pastorek, Jaromir; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2351 - 2356]

15
[ 138-39-6 ]
[ 57133-29-6 ]
[ 858368-18-0 ]

Reference： [1]Chemical Communications,2005,p. 2549 - 2551

16
[ 138-39-6 ]
[ 35444-44-1 ]
[ 928211-28-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In dichloromethane; acetonitrile at 20℃; for 19h;

Reference： [1]Krishnamurthy, Vijay M.; Semetey, Vincent; Bracher, Paul J.; Shen, Nan; Whitesides, George M. [Journal of the American Chemical Society, 2007, vol. 129, # 5, p. 1312 - 1320]

17
[ 138-39-6 ]
[ 171489-59-1 ]
C₂₈H₂₄N₄O₆S [ No CAS ]

Reference： [1]Patent: US2003/225094,2003,A1 .Location in patent: Page 12

18
[ 138-39-6 ]
[ 483324-01-2 ]
[ 1114991-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 90℃; for 12h;	To 0.1 M NMP solution of 1 equiv. of 2-chloro-4-aryl/heteroaryl-pyrimidine is added 1.2 equiv. of 4-aminomethyl-benzenesulfonamide and 5 equiv. of i-Pr2NEt. After heating at 90 C. for 12 h, the reaction is cooled to 23 C. and 10 ml of H2O was added. The mixture is extracted with 3×5 ml of ethyl acetate, and the combined organics are washed with 4×5 ml of H2O, and evaporated to yield an orange viscous oil. Purification by RP-HPLC as outlined in Procedure A, Step 2 gives the title compounds.

Reference： [1]Patent: US2009/48282,2009,A1 .Location in patent: Page/Page column 16

19
[ 138-39-6 ]
[ 21286-54-4 ]
[ 1286246-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	General procedure: Reactions of (1R)-(-)-10-camphorsulfonyl chloride 1 and (1S)-(+)-10-camphorsulfonyl chloride 2 (0.3 g,1.0 equiv) with amino derivatives 3 - 7 (1.0 equiv) were carried out at 0 C to room temperature in Schotten-Baumann conditions under nitrogen atmosphere, in the presence of a stoichiometric amount of dropwised dry TEA (1.0 equiv for 3, 5, 6 and 2.0 equiv for 4, 7), in dry DMF as solvent (2 ml). When complete (monitoring by TLC), reactions were quenched with crushed ice, extracted with ethyl acetate (20 ml), washed with 1 N HCl (2 x 10 ml) and brine (2 x 10 ml). The collected organic phase was dried on anhydrous Na2SO4, filtered and evaporated under vacuum. The crude was purified by silica gel column chromatography eluting with n-hexane/ethyl acetate or DCM/methanol to afford compounds 8-17 as white solids in medium yields.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1334 - 1337

20
[ 138-39-6 ]
[ 14152-97-7 ]
[ 1370612-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 2h;	4.1.1. General procedure 1: Synthesis of glycoconjugate benzene sulfonamides (9-24) General procedure: To a solution of per-O-acetylated isothiocyanate derivative 5-8 (1.0 equiv) in acetonitrile was added sulfonamide 1-4 (1.0 equiv for 2 and 3, 2 equiv for 1 and 4) and DIPEA (1.0 equiv, for 2 only). The reaction was stirred at 40 °C until the starting material was consumed as evidenced by TLC (2 h for 2 and 3, 1-2 days for 1 and 4). The reaction mixture was then cooled to room temperature, concentrated and the residue diluted in ethyl acetate and washed with 1.0 M aqueous HCl (3×) and water (1×). The aqueous extracts were combined and back extracted with ethyl acetate (1×). The organic extracts were combined, dried over MgSO4, filtered and evaporated. If necessary the product was purified by column chromatography (eluant 2:1 to 1:3 hexanes-EtOAc) to give 64-98 % yields.

Reference： [1]Location in patent: experimental part Moeker, Janina; Teruya, Kanae; Rossit, Sabine; Wilkinson, Brendan L.; Lopez, Marie; Bornaghi, Laurent F.; Innocenti, Alessio; Supuran, Claudiu T.; Poulsen, Sally-Ann [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2392 - 2404]

21
[ 138-39-6 ]
[ 32703-79-0 ]
[ 1429784-75-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2601 - 2605

22
[ 138-39-6 ]
[ 4744-50-7 ]
[ 1429784-83-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2601 - 2605

23
[ 138-39-6 ]
[ 22813-32-7 ]
[ 1383370-95-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 8512 - 8520

24
[ 40724-47-8 ]
[ 138-39-6 ]

Reference： [1]Patent: WO2014/144871,2014,A1

25
[ 138-39-6 ]
[ 107-85-7 ]
[ 28659-87-2 ]
C₂₀H₃₄N₅O₇Pol [ No CAS ]
C₂₄H₂₈N₂ [ No CAS ]
[ 79-08-3 ]
[ 100-46-9 ]
C₅₅H₈₇N₁₂O₁₅PolS₂ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2015,vol. 17,p. 49 - 59

26
[ 138-39-6 ]
[ 27200-79-9 ]
[ 79099-07-3 ]
tert-butyl 4-((4-bromophenethyl)(4-sulfamoylbenzyl)amino)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: tert-butyl 4-((4-bromophenethyl)(4-sulfamoylbenzyl) mino)piperidine-l-carboxylate. The title compound was obtained in a manner described in Procedure 1A from N-Boc- piperid-4-one, <strong>[27200-79-9](4-bromophenyl)acetaldehyde</strong>, and 4-aminomethylbenzenesulfonamide. ESI-MS for C25H34BrN304S calculated 552.54, found 552.6/554.6 (M+1), 550.5/552.5 (M-1)/ Procedure 1A To the solution of N-Boc-piperid-4-one in dichloroethane (DCE) (2 mL/mmol) or in DCE/AcOH (10: 1 v/v, 2 mL/mmol), a primary alkyl amine R-NH2 (1 equiv), substituted by a polar functionality on the alkyl group (e.g., carboxylic acid, ester, sulfonamide, nitrile, tetrazole, etc.), is added, followed by addition of NaBH(OAc)3 (2 equiv). The reaction mixture is stirred for an appropriate period of time (typically 1 - 15 hours) at room temperature, and (4-(halo)- phenyl)acetaldehyde (1.5 equiv) is then added, followed by another portion of NaBH(OAc)3 (2 equiv). The reaction mixture is stirred for another 5 hours at room temperature after which time it is partitioned between 5% NaHC03 and EtOAc (10 mL/mmol). The organic layer is washed once again with 5% NaHC03, then brine (2x) and then is dried over MgSCu. After filtration of the drying agent and stripping the solvent, the desired product is purified either by crystallization or by flash column chromatography over silica gel.

Reference： [1]Patent: WO2016/99311,2016,A1 .Location in patent: Page/Page column 56; 71

27
[ 138-39-6 ]
[ 27200-79-9 ]
[ 79099-07-3 ]
tert-butyl 4-((4-(N-acetylsulfamoyl)benzyl)(4-bromophenethyl)amino)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/99311,2016,A1

28
[ 138-39-6 ]
[ 331-39-5 ]
(E)-3-(3,4-dihydroxyphenyl)-N-(4-sulfamoylbenzyl)acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.5%	Stage #1: caffeic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 4-homosulfanilamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16.33h;	21 (E)-3-(3,4-dihydroxyphenyl)-N-(4-sulfamoylbenzyl)acrylamide Caffeic acid (200 mg, 1.11 mmol), HOBt (150 mg, 1.11 mmol) and EDCI (212 mg, 1.11 mmol) were dissolved in DMF (3 mL) and the mixture was stirred at room temperature for 20 minutes. After 20 minutes, 4-aminomethylbenzenesulfonamide (207 mg, 1.11 mmol) was added and the mixture was stirred at room temperature for 20 minutes. After 20 min DIPEA (0.39 mL, 2.22 mmol) was added and stirred for 16 h before extraction with EtOAc, water, 1N-HCl and brine. The organic layer was dried over anhydrous Mg2SO4, concentrated under reduced pressure and purified by column chromatography. Yield 89.5%
89.5%	Stage #1: caffeic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 4-homosulfanilamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #3: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h;	21 21. Synthesis Example 21: (E)-3-(3,4-dihydroxyphenyl)-N-(4-sulfamoylbenzyl)acrylamide Caffeic acid (200 mg, 1.11 mmol), HOBt (150 mg, 1.11 mmol) and EDCI (212 mg, 1.11 mmol) were dissolved in DMF (3 mL), followed by stirring at room temperature for 20 minutes. After 20 minutes, 4-aminobenzylbenzenesulfonamide (207 mg, 1.11 mmol) was added, followed by stirring at room temperature for 20 minutes. After 20 minutes, DIPEA (0.39 mL, 2.22 mmol) was added and stirred for 16 hours, followed by extraction with EtOAc, water, 1N-HCl and brine. The organic layer was dried over anhydrous Mg2SO4, concentrated under reduced pressure, and purified by column chromatography.Yield 89.5%
	Stage #1: caffeic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 4-homosulfanilamide In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #3: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	General Procedure for Synthesis of CGA Derivatives (5 - 10) General procedure: To a solution of caffeic acid (1.0 equiv.), HOBt (1.0 equiv.) and EDCI (1.0 equiv.) in DMF were stirred at room temperature for 15 min. To this solution was added amine derivative (1.0 equiv.) and the reaction mixture was stirred at room temperature. After 15 min the reaction mixture was treated with DIPEA (2.0 equiv.) stirred at room temperature for 16 h. The reaction progress is monitored by TLC and then it was quenched with 1N HCl and extracted with EtOAc (3 x 15 mL), the organic layer was dried over MgSO4, filtered, concentrated in vacuo. The residue was purified by silica gel column chromatography (10-25% EtOAc/hexanes) to afford desired products in good yields (5-90%).

Reference： [1]Current Patent Assignee: CHUNGBUK NATIONAL UNIVERSITY - KR101693033, 2017, B1 Location in patent: Paragraph 0277; 0278; 0279; 0280
[2]Current Patent Assignee: CHUNGBUK NATIONAL UNIVERSITY - KR101624340, 2016, B1 Location in patent: Paragraph 0240-0243
[3]Jo, Hyeju; Choi, Minho; Sim, Jaeuk; Viji, Mayavan; Li, Siyuan; Lee, Young Hee; Kim, Youngsoo; Seo, Seung-Yong; Zhou, Yuanyuan; Lee, Kiho; Kim, Wun-Jae; Hong, Jin Tae; Lee, Heesoon; Jung, Jae-Kyung [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3374 - 3377]

29
[ 138-39-6 ]
[ 3027-38-1 ]
4-((5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)methyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium acetate; acetic acid for 12h; Reflux;	4.3 General procedure for the synthesis of cyclic imides 6-12 General procedure: A mixture of benzenesulfonamide (5.0 mmol), anhydroussodium acetate (0.82 g, 10.0 mmol) and an appropriate acid anhydride(5.0 mmol) in glacial acetic acid (15 mL) was heated underreflux for 12 h. After cooling of the reaction mixture, the precipitateobtained was filtered, washed with water, dried and re-crystallisedfrom an appropriate solvent.4.1.1.3 4-((5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)methyl)benzenesulfonamide (8) fx4 M.p 238-240°, 84% yield (CH3OH); IR (KBr, cm-1) ν: 3468 (NH), 1774, 1703 (C=O), 1397, 1218 (O=S=O); 1H NMR (500 MHz, CDCl3/DMSO-d6): δ 5.33 (s, 2H), 7.32 (s, 2H), 7.57-7.59 (d, 2H, J = 8.5 Hz), 7.75-7.77 (t, 2H, J = 5.0, 3.5 Hz), 8.06-8.09 (t, 1H, J = 7.5 Hz), 8.69-8.71 (d, 1H, J = 7.0 Hz), 8.80-8.81 (d, 1H, J = 8.5 Hz), 8.97 (s, 1H), 9.51 (s, 1H); 13C NMR (125 MHz, CDCl3/DMSO-d6): δ 43.52, 122.99, 123.60, 124.43, 126.24, 128.29, 129.76, 130.22, 130.40, 131.39, 134.66, 137.04, 141.38, 143.39, 146.31, 162.94, 163.41; Ms, [C19H13N3O6S: M+1, 412].

Reference： [1]Angeli, Andrea; Abdel-Aziz, Alaa A.-M.; Nocentini, Alessio; El-Azab, Adel S.; Gratteri, Paola; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5373 - 5379]

30
[ 138-39-6 ]
[ 3482-49-3 ]
N-(4-sulfamoylbenzyl)fusidic acid amide [ No CAS ]

Reference： [1]MedChemComm,2019,vol. 10,p. 961 - 969

31
[ 138-39-6 ]
[ 58758-45-5 ]
4-(((3-methoxy-2-(prop-2-yn-1-yloxy)benzylidene)amino)methyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol; chloroform at 60℃; for 18h;	4.2.2. Synthesis of compounds 6a-i General procedure: 1 mmol of 4-(aminomethyl)benzenesulfonamide and 1.1 mmolof aldehyde derivatives were dissolved in 50mL of CHCl3:MeOH(5:1, v/v). The solution was refluxed for 18 h. It was cooled andevaporated under vacuum. The pure imine compounds were obtainedafter washed by ether [25].

Reference： [1]Zengin Kurt, Belma; Sonmez, Fatih; Ozturk, Dilek; Akdemir, Atilla; Angeli, Andrea; Supuran, Claudiu T. [European Journal of Medicinal Chemistry, 2019, vol. 183]

32
[ 138-39-6 ]
[ 5651-83-2 ]
4-(((3-methoxy-4-(prop-2-yn-1-yloxy)benzylidene)amino)methyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In methanol; chloroform at 60℃; for 18h;	4.2.2. Synthesis of compounds 6a-i General procedure: 1 mmol of 4-(aminomethyl)benzenesulfonamide and 1.1 mmolof aldehyde derivatives were dissolved in 50mL of CHCl3:MeOH(5:1, v/v). The solution was refluxed for 18 h. It was cooled andevaporated under vacuum. The pure imine compounds were obtainedafter washed by ether [25].

Reference： [1]Zengin Kurt, Belma; Sonmez, Fatih; Ozturk, Dilek; Akdemir, Atilla; Angeli, Andrea; Supuran, Claudiu T. [European Journal of Medicinal Chemistry, 2019, vol. 183]

33
[ 138-39-6 ]
[ 5006-44-0 ]
6-methyl-4-oxo-N-(4-sulfamoylbenzyl)-4H-chromene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 6-Methyl-4-oxo-4H-1-benzopyran-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 80 - 90℃; for 1.2h; Stage #2: 4-homosulfanilamide In N,N-dimethyl-formamide for 1h; Heating;

Reference： [1]Angeli, Andrea; Kartsev, Victor; Petrou, Anthi; Pinteala, Mariana; Brovarets, Volodymyr; Slyvchuk, Sergii; Pilyo, Stepan; Geronikaki, Athina; Supuran, Claudiu T. [International Journal of Molecular Sciences, 2021, vol. 22, # 10]

34
[ 138-39-6 ]
[ 5006-45-1 ]
6-chloro-4-oxo-N-(4-sulfamoylbenzyl)-4H-chromene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 6-chloro-4-oxo-4H-chromene-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 80 - 90℃; for 1.2h; Stage #2: 4-homosulfanilamide In N,N-dimethyl-formamide for 1h; Heating;

35
[ 138-39-6 ]
[ 5334-48-5 ]
4-(((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)methyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium carbonate In acetonitrile at 80℃;	2.38.4 Step 4: A solution of 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (100 mg, 0.4 mmol), 4-(aminomethyl)benzenesulfonamide (145.2 mg, 0.6 mmol) and K2CO3 (180 mg, 1.3 mmol) in ACN (5 mL) was stirred at 80oC overnight. The reaction mixture was neutralized to pH = 7 and filtered. The filtrate was concentrated and purified by prep-HPLC (NH4HCO3) to give 4-(((1-phenyl- 1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)methyl)benzenesulfonamide (89.3 mg, yield: 54%) as a white solid.1HNMR (400 MHz, DMSO-d6): δ = 9.09-9.06 (m, 1H), 8.45 (s, 1H), 8.45 (s, 1H), 8.19 (d, J = 8 Hz, 2H), 7.79 (d, J = 8.4 Hz, 2H), 7.57-7.54 (m, 4H), 7.37-7.32 (m, 3H), 4.85 (d, J = 6 Hz, 2H). MS: m/z 381.0 (M+H+).

Reference： [1]Current Patent Assignee: SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE - WO2021/133915, 2021, A1 Location in patent: Paragraph 00401

36
[ 138-39-6 ]
[ 87412-89-3 ]
4-(((1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)methyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.1 mg	With potassium carbonate In acetonitrile at 80℃;	2.45.3 Step 3: A mixture of 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidine (200 mg, 1.09 mmol), K2CO3 (451 mg, 3.27 mmol) and 4-(aminomethyl)benzenesulfonamide (489 mg, 2.19 mmol) in ACN (10 mL) was stirred at 80oC overnight. The mixture was filtered and the filtrate was purified by prep-HPLC to give 4-(((1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)methyl)- benzenesulfonamide (2.1 mg) as a white solid.1HNMR (400 MHz, DMSO-d6): δ = 8.17 (s, 1H), 7.87 (t, J = 6.0 Hz, 1H), 7.75 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 6.8 Hz, 2H), 7.29 (s, 2H), 4.80 (d, J = 4.0 Hz, 2H), 3.81 (s, 3H), 2.59 (s, 3H). MS: m/z 332.9 (M+H+).

Reference： [1]Current Patent Assignee: SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE - WO2021/133915, 2021, A1 Location in patent: Paragraph 00422

37
[ 138-39-6 ]
[ 1190379-86-2 ]
4-(((2-chloro-5-cyclopropylpyrimidin-4-yl)amino)methyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With N-ethyl-N,N-diisopropylamine In ethanol at -10 - 50℃; for 16h;

Reference： [1]Drewry, David H.; Annor-Gyamfi, Joel K.; Wells, Carrow I.; Pickett, Julie E.; Dederer, Verena; Preuss, Franziska; Mathea, Sebastian; Axtman, Alison D. [Journal of Medicinal Chemistry, 2022, vol. 65, # 2, p. 1313 - 1328]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 138-39-6 ] {[proInfo.proName]}

Quality Control of [ 138-39-6 ]

Related Doc. of [ 138-39-6 ]

Product Details of [ 138-39-6 ]

Safety of [ 138-39-6 ]

Application In Synthesis of [ 138-39-6 ]

[ 138-39-6 ] Synthesis Path-Upstream 1~10

[ 138-39-6 ] Synthesis Path-Downstream 1~37

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

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