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Anti-infection
Antibacterial
Mafenide HCl
Inhibitors/Agonists
Anti-infection
Metabolic Enzyme
Antibacterial
Carbonic Anhydrase

[ CAS No. 138-37-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 138-37-4
Chemical Structure| 138-37-4
Structure of 138-37-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 138-37-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 138-37-4 ]

SDS Specification
Alternatived Products of [ 138-37-4 ]

Product Details of [ 138-37-4 ]

CAS No. :138-37-4 MDL No. :MFCD00013005
Formula : C7H11ClN2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :SIACJRVYIPXFKS-UHFFFAOYSA-N
M.W : 222.69 Pubchem ID :67313
Synonyms :
Mafenide hydrochloride;4-Aminomethylbenzenesulfonamide hydrochloride
Chemical Name :4-(Aminomethyl)benzenesulfonamide hydrochloride

Calculated chemistry of [ 138-37-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.07
TPSA : 94.56 Ų

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) : -7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.11
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 0.12
Log Po/w (SILICOS-IT) : -0.43
Consensus Log Po/w : 0.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.5
Solubility : 7.05 mg/ml ; 0.0317 mol/l
Class : Very soluble
Log S (Ali) : -1.65
Solubility : 4.97 mg/ml ; 0.0223 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.01
Solubility : 2.18 mg/ml ; 0.00977 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 138-37-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280 UN#:N/A
Hazard Statements:H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 138-37-4 ]

* 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.

  • Downstream synthetic route of [ 138-37-4 ]

[ 138-37-4 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 129363-88-8 ]
  • [ 138-37-4 ]
  • 1-(4-sulfamoyl-benzyl)-pyrrole-2,5-dicarboxylic acid diethyl ester [ No CAS ]
Reference： [1]Justus Liebigs Annalen der Chemie,1951,vol. 571,p. 44,55
  • 2
  • [ 138-37-4 ]
  • [ 23926-59-2 ]
  • [ 33645-55-5 ]
Reference： [1]Pharmazie,1971,vol. 26,p. 469 - 473
  • 3
  • [ 138-37-4 ]
  • [ 23926-60-5 ]
  • L-2-Acetylamino-2-carbethoxyethan-N-homosulfanilylamidosulfonamid [ No CAS ]
Reference： [1]Pharmazie,1971,vol. 26,p. 469 - 473
  • 4
  • [ 35444-44-1 ]
  • [ 138-37-4 ]
  • [ 928211-28-3 ]
Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 126 - 133
  • 5
  • [ 138-37-4 ]
  • sodium 3,5-bis(bis((ethoxycarbonyl)methyl)aminomethyl)benzoate [ No CAS ]
  • [ 662165-89-1 ]
Reference： [1]Chemical Communications,2003,p. 2328 - 2329
  • 6
  • [ 138-37-4 ]
  • [ 948054-25-9 ]
  • [ 2393-24-0 ]
Reference： [1]Synthesis,2007,p. 1819 - 1822
  • 7
  • [ 138-37-4 ]
  • [ 2393-24-0 ]
Reference： [1]Synthesis,2007,p. 1819 - 1822
  • 8
  • [ 138-37-4 ]
  • 4-[(4,6-diamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 9
  • [ 138-37-4 ]
  • 4-[(4,6-bis-dimethylamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 10
  • [ 138-37-4 ]
  • 4-[(4,6-dihydrazino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 11
  • [ 138-37-4 ]
  • 4-[(4,6-bis-ethylamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 12
  • [ 138-37-4 ]
  • 4-[(4,6-bis-isopropylamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 13
  • [ 138-37-4 ]
  • 2-[4-chloro-6-(4-sulfamoylbenzylamino)-1,3,5-triazin-2-ylamino]acetic acid [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3105 - 3119
  • 14
  • [ 138-37-4 ]
  • 4-[4,6-bis-(methyl-propyl-amino)-[1,3,5]triazin-2-ylamino]-methyl}-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 15
  • [ 138-37-4 ]
  • 4-[(4,6-bis-propylamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 16
  • [ 138-37-4 ]
  • 4-[(4,6-bis-diethylamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 17
  • [ 138-37-4 ]
  • 4-[(4,6-diphenoxy-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 18
  • [ 138-37-4 ]
  • 4-[(4,6-bis-butylamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 19
  • [ 138-37-4 ]
  • 4-[4,6-bis-(2-piperazin-1-yl-ethylamino)-[1,3,5]triazin-2-ylamino]-methyl}-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 20
  • [ 138-37-4 ]
  • 4-({4,6-bis-[(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethyl)-amino]-[1,3,5]triazin-2-ylamino}-methyl)-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3102 - 3108
  • 21
  • [ 138-37-4 ]
  • 4-[(4,6-dimethoxy-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonic acid amide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5427 - 5433
  • 22
  • [ 138-37-4 ]
  • 4-[(4,6-dihydroxy-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5427 - 5433
  • 23
  • [ 138-37-4 ]
  • 4-[(4,6-bis-methylamino-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5427 - 5433
  • 24
  • [ 138-37-4 ]
  • 4-[(4,6-diethoxy-[1,3,5]triazin-2-ylamino)-methyl]-benzenesulfonamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5427 - 5433
  • 25
  • [ 138-37-4 ]
  • [ 662165-83-5 ]
Reference： [1]Chemical Communications,2003,p. 2328 - 2329
  • 26
  • [ 138-37-4 ]
  • [ 142319-48-0 ]
Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 126 - 133
  • 27
  • [ 138-37-4 ]
  • (3-{3-(3-Carboxymethylsulfanyl-propoxy)-2-(3-carboxymethylsulfanyl-propoxymethyl)-2-[5-(4-sulfamoyl-benzylcarbamoyl)-pentanoylamino]-propoxy}-propylsulfanyl)-acetic acid [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 126 - 133
  • 28
  • [ 138-37-4 ]
  • [ 1026943-13-4 ]
Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 126 - 133
  • 29
  • [ 138-37-4 ]
  • [ 24488-86-6 ]
Reference： [1]Arzneimittel-Forschung/Drug Research,1974,vol. 24,p. 363 - 374
  • 30
  • [ 138-37-4 ]
  • [ 25046-88-2 ]
Reference： [1]Arzneimittel-Forschung/Drug Research,1974,vol. 24,p. 363 - 374
  • 31
  • [ 138-37-4 ]
  • [ 24489-27-8 ]
Reference： [1]Arzneimittel-Forschung/Drug Research,1974,vol. 24,p. 363 - 374
  • 32
  • [ 138-37-4 ]
  • [ 25046-89-3 ]
Reference： [1]Arzneimittel-Forschung/Drug Research,1974,vol. 24,p. 363 - 374
  • 33
  • [ 138-37-4 ]
  • [ 25046-90-6 ]
Reference： [1]Arzneimittel-Forschung/Drug Research,1974,vol. 24,p. 363 - 374
  • 34
  • [ 138-37-4 ]
  • [ 24489-29-0 ]
Reference： [1]Arzneimittel-Forschung/Drug Research,1974,vol. 24,p. 363 - 374
  • 35
  • [ 138-37-4 ]
  • L-2-Acetylamino-2-carboxyethan-N-homosulfanilylamidosulfonamid [ No CAS ]
Reference： [1]Pharmazie,1971,vol. 26,p. 469 - 473
  • 36
  • [ 138-37-4 ]
  • [ 33645-56-6 ]
Reference： [1]Pharmazie,1971,vol. 26,p. 469 - 473
  • 37
  • [ 138-37-4 ]
  • L-2-Amino-2-carboxyethan-N-homosulfanilylamidosulfonamid [ No CAS ]
Reference： [1]Pharmazie,1971,vol. 26,p. 469 - 473
  • 38
  • S-chloroacetyl-t-butyl mercaptan [ No CAS ]
  • [ 20260-53-1 ]
  • [ 138-37-4 ]
  • [ 256346-26-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; Exemplary means to synthesize the thiolester compounds represented by Templates I, II and III follow. As discussed above, the skilled artisan can use any synthetic scheme or any variation to an exemplary protocol to generate a thiolester of the invention. [00091] In templates II and IIIb, where X is CH2, CH2CH2 and CH2C(=O)NH, the thiolester can be generated using methods for synthesizing compounds 23D, 24D and 25D, respectively, described above (see Table 1). [00092] Where the thiolester is N-[2-(?-Pyridinio-4-toluoylthio)benzoyl]sulfacetamide chloride, a solution of N-(2-mercaptobenzoyl)sulfacetamide (see synthesis compound 44) (0.4 g) and 4-(chloromethyl)benzoyl chloride (0.6 ml) in dimethylacetamide (2 ml) was stirred under nitrogen for 1 h, and then added to ethyl ether (40 ml) with stirring. The viscous liquid precipitate was diluted with dimethylformamide (1 ml), and then added to a solution of ether (40 ml) and heptane (40 ml). The viscous liquid precipitate was collected and added to pyridine (3 ml). The solution was stirred at RT under Ar for 3 days, and then added to ether (50 ml). The precipitate was collected and dried. The crude product was purified on a silica gel column using isocratic elution with 10% AcOH in MeOH. [00093] Where the thiolester is N-[2-(2-(Pyridinioacetamido)benzoylthio)benzoyl]sulfacetamide chloride, an analog of compound 37 was prepared in the same manner except that chloroacetyl chloride was substituted for 3-chloropropionyl chloride. This product was dissolved in pyridine and allowed to stand at RT, and the product was worked up as described above for N-[2-(?-Pyridinio-4-toluoylthio)benzoyl]sulfacetamide chloride. [00094] Where the thiolester is N-[2-(Pyridinio acetamido acetylthio)benzoyl]sulfacetamide chloride, N-(2-Mercaptobenzoyl)sulfacetamide is prepared as described for compound 44. Chloroacetylglycine may be linked to the thiol group of this product following activation of the glycine carbonyl group via (a) a p-nitrophenyl ester derivative, or (b) an acid chloride prepared using oxalyl chloride. Workup and subsequent reaction with pyridine is carried out as described for N-[2-(?-Pyridinio-4-toluoylthio)benzoyl]sulfacetamide chloride, described above. [00095] Where the thiolester is N-[2-(2-(Pyridinioacetamido)isobutyrylthio)benzoyl]sulfacetamide chloride, the compound can be prepared in a similar manner as is N-[2-(Pyridinio acetamido acetylthio)benzoyl]sulfacetamide chloride, described above, except that N-chloroacetyl-2-aminoisobutyric acid (prepared according to Birnbaum (1952) J. Biol. Chem. 194:455 and Ronwin (1953) J. Org. Chem. 18:127,) is substituted for chloro-acetylglycine. [00096] Where the thiolester is N-[2-(5-Dimethylsulfoniovaleroylthio)benzoyl]sulfacetamide iodide, wherein Z=S+(CH3)2 and Y=(CH2)4: a mixture of compound 44 (1.10 g) and NaI (5 g) in acetone (99.9%, 25 ml) was stirred under nitrogen at RT overnight, and then added to water (250 ml) with stirring. The white precipitate was collected and dried. Yield, 1.2 g. A clear solution of this product (0.3 g) in acetonitrile (3 ml) and methyl sulfide (4 ml) was stirred at RT overnight. The clear solution was added to ethyl ether (250 ml) with vigorous stirring. The white precipitate was collected, washed with ether, and dried. Yield, 0.15 g. [00097] Where the thiolester is N-[2-(5-Triethyl ammoniovaleroylthio)benzoyl]sulfacetamide iodide, wherein Z=N+(C2H5)3 and Y=(CH2)4: a parallel synthesis to N-[2-(5-Dimethylsulfoniovaleroylthio)benzoyl]sulfacetamide iodide may be conducted wherein triethylamine is substituted for methyl sulfide. Refluxing may be required to finish reaction with triethylamine. [00098] Where the thiolester is N-[2-(5-Tri-n-butylphosphonio valeroylthio)benzoyl]sulfacetamide iodide, wherein Z=P+(C4H9)3 and Y=(CH2)4: a parallel synthesis to N-[2-(5-Dimethylsulfoniovaleroylthio)benzoyl]sulfacetamide iodide may be conducted wherein tri-n-butylphosphine is substituted for methyl sulfide. [00099] To synthesize a thiolester specie of Template III, where G is t-butyl, Y is CH2, X is CH2, the pyridine ring bears a substituted carboxamide group at R8 and R10, R6 is H, R9 is=SO2NH2, and R7, R8, R10, R11 is H: 4-[1-(t-Butylthiocarbonylmethyl)nicotinamidomethyl]-benzenesulfonamide chloride triethylamine (36 mmol) and nicotinoyl chloride hydrochloride (30 mmol) were added to a suspension of <strong>[138-37-4]4-(aminomethyl)benzenesulfonamide hydrochloride</strong> hydrate (30 mmol) in 150 ml acetonitrile. An additional 60 mmol of triethylamine were added gradually. The precipitate of 4-(nicotinamidomethyl)benzenesulfonamide was recrystallized from a solution of 12 ml ethanol in 180 ml water. Product dried in vacuo/CaCl2. Next, S-chloroacetyl-t-butyl mercaptan is prepared by reacting chloroacetyl chloride and t-butyl mercaptan according to Dawson (1947) J. Amer. Chem. Soc. 69:1211. The thiolester is generated by stirring 10 mmol of the nicotinamide derivative with 20 mmol of the chloroacetyl thioester in 125 ml acetonitr...
Reference： [1]Patent: US6706729,2004,B1 .Location in patent: Page/Page column 15-17
  • 39
  • [ 20260-53-1 ]
  • [ 138-37-4 ]
  • [ 256346-26-6 ]
YieldReaction ConditionsOperation in experiment
Exemplary means to synthesize the thiolester compounds represented by Templates I, II and III follow. As discussed above, the skilled artisan can use any synthetic scheme or any variation to an exemplary protocol to generate a thiolester of the invention. [00091] In templates II and IIIb, where X is CH2, CH2CH2 and CH2C(=O)NH, the thiolester can be generated using methods for synthesizing compounds 23D, 24D and 25D, respectively, described above (see Table 1). [00092] Where the thiolester is N-[2-(?-Pyridinio-4-toluoylthio)benzoyl]sulfacetamide chloride, a solution of N-(2-mercaptobenzoyl)sulfacetamide (see synthesis compound 44) (0.4 g) and 4-(chloromethyl)benzoyl chloride (0.6 ml) in dimethylacetamide (2 ml) was stirred under nitrogen for 1 h, and then added to ethyl ether (40 ml) with stirring. The viscous liquid precipitate was diluted with dimethylformamide (1 ml), and then added to a solution of ether (40 ml) and heptane (40 ml). The viscous liquid precipitate was collected and added to pyridine (3 ml). The solution was stirred at RT under Ar for 3 days, and then added to ether (50 ml). The precipitate was collected and dried. The crude product was purified on a silica gel column using isocratic elution with 10% AcOH in MeOH. [00093] Where the thiolester is N-[2-(2-(Pyridinioacetamido)benzoylthio)benzoyl]sulfacetamide chloride, an analog of compound 37 was prepared in the same manner except that chloroacetyl chloride was substituted for 3-chloropropionyl chloride. This product was dissolved in pyridine and allowed to stand at RT, and the product was worked up as described above for N-[2-(?-Pyridinio-4-toluoylthio)benzoyl]sulfacetamide chloride. [00094] Where the thiolester is N-[2-(Pyridinio acetamido acetylthio)benzoyl]sulfacetamide chloride, N-(2-Mercaptobenzoyl)sulfacetamide is prepared as described for compound 44. Chloroacetylglycine may be linked to the thiol group of this product following activation of the glycine carbonyl group via (a) a p-nitrophenyl ester derivative, or (b) an acid chloride prepared using oxalyl chloride. Workup and subsequent reaction with pyridine is carried out as described for N-[2-(?-Pyridinio-4-toluoylthio)benzoyl]sulfacetamide chloride, described above. [00095] Where the thiolester is N-[2-(2-(Pyridinioacetamido)isobutyrylthio)benzoyl]sulfacetamide chloride, the compound can be prepared in a similar manner as is N-[2-(Pyridinio acetamido acetylthio)benzoyl]sulfacetamide chloride, described above, except that N-chloroacetyl-2-aminoisobutyric acid (prepared according to Birnbaum (1952) J. Biol. Chem. 194:455 and Ronwin (1953) J. Org. Chem. 18:127,) is substituted for chloro-acetylglycine. [00096] Where the thiolester is N-[2-(5-Dimethylsulfoniovaleroylthio)benzoyl]sulfacetamide iodide, wherein Z=S+(CH3)2 and Y=(CH2)4: a mixture of compound 44 (1.10 g) and NaI (5 g) in acetone (99.9%, 25 ml) was stirred under nitrogen at RT overnight, and then added to water (250 ml) with stirring. The white precipitate was collected and dried. Yield, 1.2 g. A clear solution of this product (0.3 g) in acetonitrile (3 ml) and methyl sulfide (4 ml) was stirred at RT overnight. The clear solution was added to ethyl ether (250 ml) with vigorous stirring. The white precipitate was collected, washed with ether, and dried. Yield, 0.15 g. [00097] Where the thiolester is N-[2-(5-Triethyl ammoniovaleroylthio)benzoyl]sulfacetamide iodide, wherein Z=N+(C2H5)3 and Y=(CH2)4: a parallel synthesis to N-[2-(5-Dimethylsulfoniovaleroylthio)benzoyl]sulfacetamide iodide may be conducted wherein triethylamine is substituted for methyl sulfide. Refluxing may be required to finish reaction with triethylamine. [00098] Where the thiolester is N-[2-(5-Tri-n-butylphosphonio valeroylthio)benzoyl]sulfacetamide iodide, wherein Z=P+(C4H9)3 and Y=(CH2)4: a parallel synthesis to N-[2-(5-Dimethylsulfoniovaleroylthio)benzoyl]sulfacetamide iodide may be conducted wherein tri-n-butylphosphine is substituted for methyl sulfide. [00099] To synthesize a thiolester specie of Template III, where G is t-butyl, Y is CH2, X is CH2, the pyridine ring bears a substituted carboxamide group at R8 and R10, R6 is H, R9 is=SO2NH2, and R7, R8, R10, R11 is H: 4-[1-(t-Butylthiocarbonylmethyl)nicotinamidomethyl]-benzenesulfonamide chloride triethylamine (36 mmol) and nicotinoyl chloride hydrochloride (30 mmol) were added to a suspension of <strong>[138-37-4]4-(aminomethyl)benzenesulfonamide hydrochloride</strong> hydrate (30 mmol) in 150 ml acetonitrile. An additional 60 mmol of triethylamine were added gradually. The precipitate of 4-(nicotinamidomethyl)benzenesulfonamide was recrystallized from a solution of 12 ml ethanol in 180 ml water. Product dried in vacuo/CaCl2. Next, S-chloroacetyl-t-butyl mercaptan is prepared by reacting chloroacetyl chloride and t-butyl mercaptan according to Dawson (1947) J. Amer. Chem. Soc. 69:1211. The thiolester is generated by stirring 10 mmol of the nicotinamide derivative with 20 mmol of the chloroacetyl thioester in 125 ml acetonitr...
Reference： [1]Patent: US6706729,2004,B1 .Location in patent: Page/Page column 15-7
  • 40
  • [ 872042-97-2 ]
  • [ 138-37-4 ]
  • C15H18N6O3S*ClH [ No CAS ]
Reference： [1]Patent: WO2005/123736,2005,A1 .Location in patent: Page/Page column 17-18; 21
  • 41
  • [ 24424-99-5 ]
  • [ 138-37-4 ]
  • [ 206265-18-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethanol; dichloromethane; 24A. Preparation of N-(4-(aminomethyl)phenylsulfonyl)acetamide; Di-tert-butyl dicarbonate (4.80 gm, 22 mmole) was added to a solution of 4-(aminomethyl)benzenesulfonamide hydrogen chloride (4.45 gm, 20 mmole) and TEA (6.14 mL, 44 mmole) in a mixture of DCM (50 mL) and EtOH (7 mL). After the reaction was complete, it was diluted with DCM, washed with water, and dried (Na2SO4). The solvent was removed to leave the crude carbamic acid, [[4-(aminosulfonyl)phenyl]methyl]-tert-butyl ester. A portion of this (1.29 gm, 4.49 mmole) was added to a stirred suspension of K2CO3 (1.24 gm, 8.99 mmole) in acetone (18 mL) followed by acetyl chloride (0.42 mL, 5.84 mmole) and the mixture was heated at refux for 16 hr. Further acetyl chloride (0.42 mL, 5.84 mole) was added and heating was continued for and additional 1.5 hr. After cooling to RT, water was added to give a clear solution which was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), and the solvent removed. Silica gel column chromatography (elution with a mixture of DCM and MeOH) afforded the carbamic acid, [[4-(N-acetyl-aminosulfonyl)phenyl]methyl]-tert-butyl ester (1.14 gm, 77%) as a solid: 1H NMR (CDCl3): 1.46 (s, 9H), 2.05 (s, 3H), 4.39 (br s, 2H), 5.0 (br s, 1H), 7.44 (d, 2H), 7.99 (d, 2H), 8.5 (br s, 1H). This (1.29 gm 3.93 mmole) was dissolved in a mixture of dry DCM (40 mL) and TFA (30 mL) in an ice bath. After 1 hr, the solvent was removed to leave the TFA salt of the final product. Material was converted to the free base by application onto a SCX column (Varian Mega Bond Elut SCX) that had been conditioned with MeOH. This was washing with 1 column volume of MeOH followed by several column volumes of a 2.0 N solution of NH3 in MeOH. Removal of the solvent from the appropriate fractions left the product as a glass: MS: 229 (M+H)+; HPLC Ret Time: 0.12 min (YMC Xterra S7 3.0×50 mm column, 3 min gradient, 4 mL/min).
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 48h; Toa solution of 4-(aminomethyl)benzenesulfonamide, hydrochloride (501.0 mg, 2.250mmol) in tetrahydrofuran (9.9 mL) was added N,N-diisopropylethylamine (786 mul,4.50 mmol) and Boc2O (575 mul, 2.475 mmol), and the solution wasstirred for 48 h. The solution wasdiluted with dichloromethane (100 mL), and washed with 1 N aq. HCl (50 mL),followed by saturated aq. NaHCO3 (50 mL). The organic phase was dried over anhydrous Na2SO4,filtered, and concentrated to afford tert-butyl 4-sulfamoylbenzylcarbamate(643.9 mg,100 % crude yield) as a white foam that was used without furtherpurification. LCMS: [M+H]+:287.3.
Reference： [1]Patent: US2006/14745,2006,A1 .Location in patent: Page/Page column 20-21
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3676 - 3680
  • 42
  • [ 138-37-4 ]
  • [ 122-04-3 ]
  • [ 50889-01-5 ]
YieldReaction ConditionsOperation in experiment
2.86 g (85%) With triethylamine; In water; acetonitrile; Synthesis of 4-[3-(3-carbaminmidoylphenyl)-ureido]-N-(4-sulfamoylbenzyl)-benzamide (84): A solution of 4-nitrobenzoylchloride (1.85 g, 1 eq.) in acetonitrile (20 ml) was added to a solution of <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (4.44 g, 2 eq.) and triethylamine (2.78 ml, 2 eq.) in acetonitrile (40 ml) at 0 C. under inert atmosphere. After the addition was completed, the mixture was warmed to rt and stirred for 3 d. Water was added and the mixture was concentrated under reduced pressure. The resulting precipitate was filtered off and washed with water and methanol to yield 2.86 g (85%) of 4-nitro-N-(4-sulfamoylbenzyl)-benzamide.
2.86 g (85%) With triethylamine; In water; acetonitrile; Synthesis of 4-[3-(3-carbamimidoylphenyl)-ureido]-N-(4-sulfamoylbenzyl)-benzamide A solution of 4-nitrobenzoylchloride (1.85 g, 1 eq.) in acetonitrile (20 ml) was added to a solution of <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (4.44 g, 2 eq.) and triethylamine (2.78 ml, 2 eq.) in acetonitrile (40 ml) at 0 C. under inert atmosphere. After the addition was completed, the mixture was warmed to rt and stirred for 3 d. Water was added and the mixture was concentrated under reduced pressure. The resulting precipitate was filtered off and washed with water and methanol to yield 2.86 g (85%) of 4-nitro-N-(4-sulfamoylbenzyl)-benzamide.
2.86 g (85%) With triethylamine; In water; acetonitrile; Synthesis of 4-[3-(3-carbaminmidoylphenyl)-ureido]-N-(4-sulfamoylbenzyl)-benzamide (84) A solution of 4-nitrobenzoylchloride (1.85 g, 1 eq.) in acetonitrile (20 ml) was added to a solution of <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (4.44 g, 2 eq.) and triethylamine (2.78 ml, 2 eq.) in acetonitrile (40 ml) at 0 C. under inert atmosphere. After the addition was completed, the mixture was warmed to rt and stirred for 3 d. Water was added and the mixture was concentrated under reduced pressure. The resulting precipitate was filtered off and washed with water and methanol to yield 2.86 g (85%) of 4-nitro-N-(4-sulfamoylbenzyl)-benzamide.
Reference： [1]Patent: US2003/119876,2003,A1
[2]Patent: US2002/165236,2002,A1
[3]Patent: US6949567,2005,B2
  • 43
  • [ 138-37-4 ]
  • [ 455901-13-0 ]
  • [3-(3-cyanophenyl)-ureido]-N-(4-sulfonamidobenzyl)-4-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.27 g (99.7%) With triethylamine; In water; acetonitrile; 4-[3-(3-Cyanophenyl)-ureido]-benzenesulfonylchloride (5.04 g, 1 eq.) was added in portions to a solution of <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (6.68 g, 2 eq.) and triethylamine (8.32 ml, 2 eq.) in acetonitrile (100 ml) at 0 C. under inert atmosphere. The mixture was warmed to rt, stirred for 3 d and then concentrated in vacuo. Water was added and the resulting precipitate filtered off and dried in vacuo. Yield: 7.27 g (99.7%) of [3-(3-cyanophenyl)-ureido]-N-(4-sulfonamidobenzyl)-4-benzenesulfonamide.
7.27 g (99.7%) With triethylamine; In water; acetonitrile; 4-[3-(3-Cyanophenyl)-ureido]-benzenesulfonylchloride (5.04 g, 1 eq.) was added in portions to a solution of <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (6.68 g, 2 eq.)and triethylamine (8.32 ml, 2 eq.) in acetonitrile (100 ml) at 0 C. under inert atmosphere. The mixture was warmed to rt, stirred for 3 d and then concentrated in vacuo. water was added and the resulting precipitate filtered off and dried in vacuo. Yield: 7.27 g (99.7%) of [3-(3-cyanophenyl)-ureido]-N-(4-sulfonamidobenzyl)-4-benzenesulfonamide.
7.27 g (99.7%) With triethylamine; In water; acetonitrile; 4-[3-(3-Cyanophenyl)-ureido]-benzenesulfonylchloride (5.04 g, 1 eq.) was added in portions to a solution of <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (6.68 g, 2 eq.) and triethylamine (8.32 ml, 2 eq.) in acetonitrile (100 ml) at 0 C. under inert atmosphere. The mixture was warmed to rt, stirred for 3 d and then concentrated in vacuo. Water was added and the resulting precipitate filtered off and dried in vacuo. Yield: 7.27 g (99.7%) of [3-(3-cyanophenyl)-ureido]-N-(4-sulfonamidobenzyl)-4-benzenesulfonamide.
Reference： [1]Patent: US2003/119876,2003,A1
[2]Patent: US2002/165236,2002,A1
[3]Patent: US6949567,2005,B2
  • 44
  • [ 607-68-1 ]
  • [ 86-96-4 ]
  • [ 138-37-4 ]
  • [ 474397-42-7 ]
YieldReaction ConditionsOperation in experiment
154 mg (88%) With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In ethanol; A15.1: 2-chloro-4-(4-aminosulfonylbenzyl)quinazoline A mixture of 2,4-dichloroquinazoline [prepared from benzoyleneurea and POCl3 by the method of Butler et al., J. Chem. Soc. 1959, 1512.] (100 mg, 0.502 mmol, 1 eq), 4-aminosulfonylbenzylamine hydrochloride (117.5 mg, 0.527 mmol, 1.05 eq) and diisopropylethylamine (0.26 mL, 1.506 mmol, 3 eq) in absolute ethanol (1.6 mL) was stirred at ambient temperature for 4 h. The precipitated solid was collected by filtration, washed with water and cold ethanol, and dried to afford 154 mg (88%) of 2-chloro-4-(4-aminosulfonylbenzyl)quinazoline as a white solid. LC/MS: 349 [M+H]+; HPLC: 96% at 1.86 min (Primesphere:5 mum C18 column 4.6*30 mm, 10-90% aqueous methanol over 2 min containing 0.2% phosphoric acid, 5 mL/min, monitoring at 254 nm); 1H NMR (400 MHz, DMSO-d6): delta9.37 (t, J=5.8 Hz, 1 H), 8.32 (d, J=8.2 Hz, 1 H), 7.85-7.53 (m, 7 H), 7.32 (s, 2 H), 4.81 (d, J=5.7 Hz, 2 H).
Reference： [1]Patent: US2003/92721,2003,A1
  • 45
  • [ 138-37-4 ]
  • [ 479072-24-7 ]
YieldReaction ConditionsOperation in experiment
77 mg (88%) With N-ethyl-N,N-diisopropylamine; In ethanol; B1.2: 4-[[[4-(Aminosulfonyl)phenyl]methyl]amino]-2-chloropyrido[2,3-d]pyrimidine A mixture of 1.1 (50 mg, 0.250 mmol, 1 eq), 4-aminosulfonylbenzylamine hydrochloride (58.5 mg, 0.262 mmol, 1.05 eq) and diisopropylethylamine (0.13 mL, 0.75 mmol, 3 eq) in absolute ethanol (1 mL) was stirred at rt for 24 h. The reaction mixture was then cooled in an ice/water bath and the solid was collected by filtration, washed with water and cold ethanol and dried to provide 77 mg (88%) of B1.2 as an off-white solid. LC/MS: 350.31 [M+H]+; HPLC: >95% at 1.01 min (Xterra 5 mum C18 column 4.6 *30 mm, 10-90% aqueous methanol over 2 min containing 0.2% phosphoric acid, 5 mL/min, monitoring at 254 nm).
Reference： [1]Patent: US2003/92721,2003,A1
  • 46
  • [ 247568-48-5 ]
  • [ 138-37-4 ]
  • [ 247568-34-9 ]
  • [ 247567-16-4 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 37 N-(4-Sulfamoylbenzyl)-2-(cyclopentylamino)-5-nitrobenzamide (162 mg) was obtained as yellow powders from 2-(cyclopentylamino)-5-nitrobenzoic acid (100 mg) and 4-sulfamoylbenzylamine hydrochloride (107 mg) in a manner similar to Preparation 1. NMR (DMSO-d6, delta): 1.38-1.52 (2H, m), 1.56-1.74 (4H, m), 1.96-2.10 (2H, m), 3.96 (1H, m), 4.50 (2H, d, J=7 Hz), 6.86 (1H, d, J=8 Hz), 7.33 (2H, s), 7.50 (2H, d, J=8 Hz), 7.78 (2H, d, J=8 Hz), 8.15 (1H, d, J=8 Hz), 8.67 (1H, d, J=4 Hz), 9.16 (1H, d, J=8 Hz), 9.50 (1H, br); Mass m/z: 417(M+).
Reference： [1]Patent: US6384080,2002,B1
  • 47
  • (Z)-methyl N,N'-dibenzoylcarbamimidothioate [ No CAS ]
  • [ 138-37-4 ]
  • [ 133278-52-1 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; EXAMPLE 57 N,N'-[[[4-(Aminosulfonyl)phenyl]methyl]carbonimidoyl]bisbenzamide A stirred mixture of 4.4 g. of 4-aminomethylbenzenesulfonamide hydrochloride, 6.0 g. of 1,3-bisbenzoyl-2-methyl-isothiourea, and 3.0 g. of sodium acetate in 500 ml. of isopropyl alcohol was refluxed for 5 hours. The mixture was filtered and 10 g. of colorless crystals were collected. Recrystallization from acetonitrile gave 4.9 g. of title compound as colorless crystals, m.p. 165-167 C.
Reference： [1]Patent: US4977189,1990,A
  • 48
  • [ 133244-68-5 ]
  • [ 138-37-4 ]
  • [ 133244-52-7 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 58 N-[[[[4-(Aminosulfonyl)phenyl]methyl]amino][(4-methylbenzoyl)amino]methylene]-4-methoxybenzamide Using the method of Example 57, the interaction of 4-aminomethylbenzenesulfonamide hydrochloride with 1-(4-methoxybenzoyl)-3-(4-methylbenzoyl)-2-methylisothiourea provides the title compound as colorless crystals, m.p. 200-203 C.
Reference： [1]Patent: US4977189,1990,A
  • 49
  • [ 463-71-8 ]
  • [ 138-37-4 ]
  • [ 51929-73-8 ]
YieldReaction ConditionsOperation in experiment
95% With concentrated hydrochloric acid; In water; EXAMPLE 1 This example illustrates a method for the preparation of 4-isothiocyanatomethyl-benzenesulfonamide (compound B). The method of McKee and Bost (McKee and Bost, 1946, supra) is modified as follows. An amount of 22.2 g (0.1 mol) of homosulfanilamide hydrochloride is dissolved in 200 mL of water and 10 mL of concentrated hydrochloric acid solution is added, together with 11.2 g (0.1 mol) of thiophosgene. Stirring is begun immediately until all the red color of thiophosgene disappears (around 3.5-4 h) and a white crystalline precipitate forms. The product is filtered and recrystallized from acetone-water (1:1, v/v). The yield is 95 % (m.p. 179-81C).
Reference： [1]Patent: EP1421935,2004,A1
  • 50
  • [ 23911-25-3 ]
  • [ 138-37-4 ]
  • {(2-{carboxymethyl-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-ethyl)-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 836 - 841
  • 51
  • [ 23911-26-4 ]
  • [ 138-37-4 ]
  • {{2-[carboxymethyl-(2-{carboxymethyl-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-ethyl)-amino]-ethyl}-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 836 - 841
  • 52
  • [ 1036738-03-0 ]
  • [ 138-37-4 ]
  • [ 1036738-09-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 90℃; for 4h;Product distribution / selectivity; A solution of 2-chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4-ol (1g, 3.63 mmol), <strong>[138-37-4]4-(aminomethyl)benzenesulfonamide hydrochloride</strong> (808mg, 3.63 mmol) and diisopropylethylamine (1.90ml, 10.89 mmol) in 1 ,4-dioxane (40 ml_) was heated at 9O0C for 4 hrs. The reaction was cooled to room temperature and concentrated in vacuo. The residue was partitioned between EtOAc and H2O. The aqueous layer was extracted twice with EtOAc. The combined organic layers were then washed with H2O and saturated aqueous NaCI solution. The organic phase was then dried over solid MgSO4, filtered and concentrated in vacuo. This gave 4-[6-(4-fluoro- phenyl)-4-hydroxy-pyrido[3,2-d]pyrimidin-2-ylamino]-methyl}-benzenesulfonamide as a brown solid after drying on high vacuum. MS (m/z) 426 [M+H]+.
Reference： [1]Patent: WO2008/77651,2008,A1 .Location in patent: Page/Page column 81
  • 53
  • [ 138-37-4 ]
  • [ 63744-24-1 ]
  • [ 1124320-70-2 ]
YieldReaction ConditionsOperation in experiment
76% With N-ethyl-N,N-diisopropylamine; In 2-methyl-propan-1-ol; at 108℃; for 3h; 4-Aminomethyl-benzenesulfonamide hydrochloride (2.22g, lOmmol) was added to a solution of 3,6,8-Tribromo-imidazo[l,2-a]pyrazine (2.77g, lOmmol) and DIPEA (3.65ml, 21mmol) in 1BuOH (20 mL). The reaction was stirred at 1080C for 3h then allowed to cool to room temperature. The precipitate formed was filtered and washed with diethyl ether to give 4-[(3,6- Dibromo-imidazo[l,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide as a pale brown solid (3.5 g, 76% yield). LC-MS m/z 462 [M+H]+.
Reference： [1]Patent: WO2009/24585,2009,A2 .Location in patent: Page/Page column 75-76
  • 54
  • [ 143591-61-1 ]
  • [ 138-37-4 ]
  • [ 1124321-32-9 ]
YieldReaction ConditionsOperation in experiment
38% With N-ethyl-N,N-diisopropylamine; In 2-methyl-propan-1-ol; at 108℃; for 16h; To a solution of 3-bromo-8-chloro-imidazo[l,2-a]pyrazine (2 g, 8.6 mmol) in 1BuOH (5 ml) is added <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (2.1 g, 9.5 mmol) and DIPEA (3.7 ml, 21.5 mmol). The reaction is heated to 108 0C and stirred for 16h. After this time the solution is allowed to cool, resulting in a thick white precipitate. The precipitate is filtered and washed with diethyl ether to give 4-[(3-Bromo-imidazo[l,2-a]pyrazin-8-ylamino)-methyl]- benzenesulfonamide as a white solid (1.24 g, 38 %).
Reference： [1]Patent: WO2009/24585,2009,A2 .Location in patent: Page/Page column 46-47
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589
  • 55
  • [ 1124321-36-3 ]
  • [ 138-37-4 ]
  • [ 1124321-37-4 ]
YieldReaction ConditionsOperation in experiment
30% With N-ethyl-N,N-diisopropylamine; In 2-methyl-propan-1-ol; at 108℃; for 16h; To a solution of 3-bromo-8-chloro-2-methyl-imidazo[l,2-a]pyrazine (0.77 g, 3.12 mmol) in 1BuOH (10 ml) is added <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (1.04 g, 4.69 mmol) and DIPEA (1.63 ml, 9.36 mmol). The reaction is heated to 108 0C and stirred for 16h. After this time the solution is allowed to cool, resulting in a thick white precipitate. The precipitate is filtered and washed with diethyl ether to give 4-[(3-Bromo-2-methyl-imidazo[l,2- a]pyrazin-8-ylamino)-methyl]-benzenesulphonamide as a white solid (0.37 g, 30 %).
Reference： [1]Patent: WO2009/24585,2009,A2 .Location in patent: Page/Page column 67-68
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589
  • 56
  • [ 1124321-39-6 ]
  • [ 138-37-4 ]
  • [ 1124321-40-9 ]
YieldReaction ConditionsOperation in experiment
67% With N-ethyl-N,N-diisopropylamine; In 2-methyl-propan-1-ol; at 108℃; for 16h; To a solution of 3-bromo-8-chloro-5-methyl-imidazo[l,2-a]pyrazine (308mg,1.25mmol) in 1BuOH (5 mL) is added <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (298mg,1.38mmol) and DIPEA (0.43ml_, 3.12mmol). The reaction is stirred at 1080C for 16h. After this time the solution is allowed to cool, resulting in a thick precipitate that is filtered and washed with diethyl ether to give 330mg of pure product as a beige solid (67%).
Reference： [1]Patent: WO2009/24585,2009,A2 .Location in patent: Page/Page column 69; 71
  • 57
  • 3-bromo-8-chloro-6-methyl-imidazo[1,2-a]pyrazine [ No CAS ]
  • [ 138-37-4 ]
  • [ 1124321-51-2 ]
YieldReaction ConditionsOperation in experiment
75% With N-ethyl-N,N-diisopropylamine; In 2-methyl-propan-1-ol; at 108℃; for 16h; To a solution of 3-bromo-8-chloro-6-methyl-imidazo[l,2-a]pyrazine (350mg, 1.42mmol) in 1BuOH (3 mL) is added <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (334mg, 1.42mmol) and DIPEA (0.49ml_, 2.82mmol). The reaction is stirred at 1080C for 16h. After this time the solution is allowed to cool, resulting in a thick precipitate that is filtered and washed with diethyl ether to give 4-[(3-bromo-6-methyl-imidazo[l,2-a]pyrazin-8-ylamino)-methyl]- benzenesulfonamide as a beige solid (420mg, 75 %).
Reference： [1]Patent: WO2009/24585,2009,A2 .Location in patent: Page/Page column 72; 74
  • 58
  • [ 138-37-4 ]
  • [ 864528-35-8 ]
Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 563 - 569
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 4288 - 4295
  • 59
  • [ 1000885-56-2 ]
  • [ 138-37-4 ]
  • [ 1000880-34-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 220℃; for 1.5h;microwave irradiation; A mixture of [6-(4-fluoro-phenyl)-2-methylsulfanyl-pteridin-4-yl]-(2,2,2-trifluoro-ethyl)-amine (55 mg, 0.15 mmol), <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (331 mg, 1.5 mmol), and DIEA (0.5 mL, 3 mmol) in NMP (1.5 mL) was heated to 220 C. for 1.5 hour using microwave irradiation. Water was added and the resulting yellow precipitate was collected by vacuum filtration. The crude solid was purified by RP HPLC using a C18 column with a gradient of H2O, 0.05% TFA-acetonitrile, to provide 26 mg of 4-[6-(4-fluoro-phenyl)-4-(2,2,2-trifluoro-ethylamino)-pteridin-2-ylamino]-methyl}-benzenesulfonamide which was characterised as follows:MS (m/z) 508.2 [M+H]+;HPLC Rt=1.99 min.; and1H-NMR (300 MHz, CD3OD) delta 4.36 (4H, m), 7.26 (2H, m), 7.55 (2H, d), 7.86 (2H, d), 8.31 (2H, m) and 9.37 (1H, s) ppm.
Reference： [1]Patent: US2009/318456,2009,A1 .Location in patent: Page/Page column 19-20
  • 60
  • [ 1000885-59-5 ]
  • [ 138-37-4 ]
  • [ 1000885-60-8 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 120℃; for 0.166667h;microwave irradiation; A mixture of 6-(4-Fluoro-phenyl)-2-methylsulfanyl-3H-pteridin-4-one (213 mg, 0.7 mmol), <strong>[138-37-4]4-aminomethyl-benzenesulfonamide hydrochloride</strong> (230 mg, 1.05 mmol) and DIEA (360 muL, 2.1 mmol) in dioxane (6 mL) was heated to 120 C. for 10 minutes using microwave irradiation. The mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness. The crude product was carried to the next step without further purification but was characterised as follows: MS (m/z) 427.1 [M+H]+; HPLC Rt=1.94 min.
Reference： [1]Patent: US2009/318456,2009,A1 .Location in patent: Page/Page column 21
  • 61
  • [ 1003-14-1 ]
  • [ 24424-99-5 ]
  • [ 138-37-4 ]
  • 4-[(2-hydroxybutylamino)methyl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% To a mixed suspension of 4-aminomethylbenzenesulfonamide hydrochloride (4.45 g), methanol (20 ml) and THF (10 ml) was added N-ethyldiisopropylamine (5.2 ml) and then 1,2-epoxybutane (2.58 ml) was added, and the mixture was heated under reflux for 12 hrs. A 1N aqueous sodium hydroxide solution was added and the reaction mixture was basified and di-t-butyl carbonate (6.55 g) was added. The mixture was stirred at room temperature for 2 hrs. The solvent was evaporated under reduced pressure, and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid, aqueous sodium hydrogen carbonate and brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=7/3?1/1). To the obtained colorless amorphous form was added 4N hydrochloric acid ethyl acetate solution (10 ml), and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure, toluene was added and the solvent was again evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue and the mixture was crystallized to give the title compound (2.58 g, 46%).1H-NMR (DMSO-d6) delta: 0.87 (3H, t, J=7.4 Hz), 1.30-1.50 (2H, m), 2.71 (1H, m), 2.94 (1H, m), 3.72 (1H, m), 4.23 (2H, s), 5.33 (1H, d, J=5.6 Hz), 7.72 (2H, d, J=8.4 Hz), 7.87 (2H, d, J=8.4 Hz), 9.15 (2H, brs).
Reference： [1]Patent: EP1484320,2004,A1 .Location in patent: Page 139-140
  • 62
  • [ 1203655-70-2 ]
  • [ 138-37-4 ]
  • [ 76-05-1 ]
  • [ 1203652-23-6 ]
YieldReaction ConditionsOperation in experiment
41% A mixture of [2-Chloro-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-4-yl]-(1- trifluoromethyl-cyclopropyl)-amine (51.6 mg) and 4-aminomethy.- benzenesulfonamide hydrochloride (51.4 mg) was dissolved in NMP (1 mL) and treated with diisopropylethylamine (0.065 mL). The reaction mixture was sealed and heated by microwave to 140 0C for 1 .5 h. The reaction mixture was cooled and purified by preparative HPLC (5-95% acetonitrile:water wth 0.1 % TFA) to afford 36 mg (41% yield) of the title compound as its TFA which was characterized by its NMR and mass spectrum as follows: 1H NMR (d6-DMSO): d 1.26 (br s, 2H)1 1.37 (br s, 2H), 4.80 (d, 2H), 7.34-7.40 (m, 4H), 7.55 (d, 2H), 7.78 (d, 2H), 7.99 (d, 1 H), 8.48 (m, 3H), 8.9 (br s, 1 H), 10.1 (br s, 1 H); MS (m/z): 533.2 ([M+Hf, 100).
Reference： [1]Patent: WO2010/2998,2010,A1 .Location in patent: Page/Page column 92-93
  • 63
  • [ 1036738-13-2 ]
  • [ 138-37-4 ]
  • [ 1036738-14-3 ]
YieldReaction ConditionsOperation in experiment
97% With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 110 - 120℃; for 3h; 2,6-Dichloro-pyrido[3,2-d]pyrimidin-4-oi (9.9 g) and 4-Aminomethyl- benzenesulfonamide hydrochloride (12 g) in NMP (80 mL) was treated with diisopropyiethySamine (17.5 mL) and heated to 1 10 0C for 2 h, followed by 120 0C for an additional 1 h. The reaction mixture was cooled to ambient temperature and slowly treated with water (120 mL) and acetic acid (3 mL). The resulting sticky solid was filtered, stirred with water (200 mL) and filtered again. After drying in vacuo, the resulting solid was stirred with acetonitre (25 mL)/ether (150 mL) to afford a fine powder which was filtered and dried to 16.2 g (97 % yield) of the desired intermediate which was used without further purification in the next step.
Reference： [1]Patent: WO2010/2998,2010,A1 .Location in patent: Page/Page column 91
  • 64
  • [ 1150566-27-0 ]
  • [ 138-37-4 ]
  • [ 1150566-31-6 ]
YieldReaction ConditionsOperation in experiment
47% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 160℃; for 11h;Microwave irradiation; Example 46-{4-Sulfamoyl-benzylamino)-imidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester; A mixture of 6-chloro-imidazo[1 ,2-b]pyridazine-3-carboxylic acid ethyl ester (0.45 g, 1.99 mmol), 4-homosulfanilamide hydrochloride (0.975 g, 4.38 mmol) and diisopropylethylamine (0.76 mL, 4.38 mmol) in 1,4-dioxane (5 mL) was heated at 1600C for 11 hours under microwave irradiation. The solvent was removed in vacuo, saturated aqueous solution of sodium hydrogen carbonate (15 mL) was added and the mixture was extracted with ethyl acetate (4 * 50 mL). The combined organic fractions were dried (sodium sulphate), the solvent removed in vacuo and the residue was purified by flash column chromatography on silica gel (ethyl acetate/methanol 10:0 to 9.5:0.5) to give 0.35 g (47% yield) of 6-(4- sulfamoyl-benzylamino)-imidazo[1 ,2-b]pyridazine-3-carboxylic acid ethyl ester as a brown solid.LCMS: 376 [M+1], (MW: 375.41).
Reference： [1]Patent: WO2009/60197,2009,A1 .Location in patent: Page/Page column 61
  • 65
  • [ 98632-99-6 ]
  • [ 138-37-4 ]
  • [ 1206635-00-8 ]
Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 1288 - 1305
  • 66
  • [ 53270-66-9 ]
  • [ 138-37-4 ]
  • [ 1219708-39-0 ]
Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2913 - 2926
  • 67
  • [ 138-37-4 ]
  • [ 20728-70-5 ]
  • [ 1219708-38-9 ]
Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2913 - 2926
  • 68
  • [ 138-37-4 ]
  • [ 314079-40-8 ]
  • [ 1219708-37-8 ]
Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2913 - 2926
  • 69
  • [ 138-37-4 ]
  • [ 6806-56-0 ]
  • [ 1219708-35-6 ]
Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2913 - 2926
  • 70
  • [ 138-37-4 ]
  • [ 6806-56-0 ]
  • [ 1219708-36-7 ]
Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2913 - 2926
  • 71
  • [ 67-56-1 ]
  • [ 4316-93-2 ]
  • [ 138-37-4 ]
  • [ 1254784-19-4 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7413 - 7421
  • 72
  • [ 4316-93-2 ]
  • [ 138-37-4 ]
  • [ 1254784-02-5 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7413 - 7421
  • 73
  • [ 138-37-4 ]
  • [ 33097-11-9 ]
  • [ 1254784-12-7 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7413 - 7421
  • 74
  • [ 138-37-4 ]
  • [ 33097-13-1 ]
  • [ 1254784-08-1 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7413 - 7421
  • 75
  • [ 1202704-64-0 ]
  • [ 138-37-4 ]
  • [ 1202699-05-5 ]
YieldReaction ConditionsOperation in experiment
15% A mixture of methyl l-cyclohexyl-5-([2-(ethyloxy)-2-oxoethyl]amino}carbonyl)-2,4- dihydroxy-6-oxo-l,6-dihydro-3-pyridinecarboxylate (250 mg, 0.631 mmoles), 4- aminomethylbenzenesulfonamide hydrochloride (156 mg, 0.701 mmoles) and diisopropylethylamine (122 muL, 0.704 mmoles) in 1,4-dioxane (3 mL) was sealed in a pressure tube and heated in a microwave reactor at 150 0C for 30 minutes. The mixture was treated with 6 molar sodium hydroxide solution (2 mL) and stirred overnight. The mixture was acidified and extracted into ethyl acetate (x2). Combined extracts were washed with 1 molar hydrochloric acid, dried and evaporated and purified by preparative HPLC (40-80%acetonitrile-water-0.1%TFA). On evaporation of the required fractions the title compound was slurried in ethanol, collected, washed <n="27"/>with ethanol and hexane, and dried to give the title compound (48 mg, 15%). 1H NMR (400 MHz, OMSO-d6) delta ppm 12.98 (s, 1 H), 9.43 - 10.40 (m, J=109.64 Hz, 2 H), 7.80 (d, J=8.34 Hz, 2 H), 7.51 (d, J=8.59 Hz, 2 H), 7.34 (s, 2 H), 4.73 - 5.00 (m, 1 H), 4.63 (d, J=6.06 Hz, 2 H), 4.08 (d, J=5.56 Hz, 2 H), 2.24 - 2.43 (m, 2 H), 1.80 (d, ./=12.88 Hz, 2 H), 1.48 - 1.70 (m, 3 H), 1.29 (q, J=13.22 Hz, 2 H), 1.13 (q, ./=12.29 Hz, 1 H).
Reference： [1]Patent: WO2009/158315,2009,A1 .Location in patent: Page/Page column 25
  • 76
  • [ 138-37-4 ]
  • [ 1311200-28-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3105 - 3119
  • 77
  • [ 138-37-4 ]
  • [ 1311200-29-9 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3105 - 3119
  • 78
  • [ 138-37-4 ]
  • [ 1311200-30-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3105 - 3119
  • 79
  • [ 138-37-4 ]
  • [ 1311200-31-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3105 - 3119
  • 80
  • [ 1119451-38-5 ]
  • [ 138-37-4 ]
  • [ 1340598-24-4 ]
YieldReaction ConditionsOperation in experiment
15% With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 20℃;Inert atmosphere; Example 9 : N-[4-(Aminosulfonyl)phenyl]methyl}-1 -(4,6-dimethyl-1 ,3- benzothiazol-2-yl)-3-piperidinecarboxamide (E9) A mixture of 1 -(4,6-dimethyl-1 ,3-benzothiazol-2-yl)-3-piperidinecarboxylic acid (for a method of preparation see, for example, Description 5) (25mg, 0.09mmol), 4- (aminomethyl)benzenesulfonamide hydrochloride (commercially available) (23mg, O.I Ommol), ), EDC hydrochloride (35mg, 0.18mmol) and 1 -hydroxy-7- azabenzotriazole (2mg, 0.018mmol) in dichloromethane : tetrahydrofuran (1 :1 , v/v, 6ml) was stirred at room temperature under argon for 3h. Then 15 mg of 4- (aminomethyl)benzenesulfonamide hydrochloride were added and the mixture was left under the same conditions overnight. The solvent was then removed in vacuo and the resulting residue was purified by MDAP. Fractions containing product were combined and the solvent was removed in vacuo to give the title compound as a white solid which was left in the high-vacuum overnight (6mg, 15%).1 H NMR (400 MHz, DMSO): delta 1 .53-1 .72 (2H,m), 1.80 (1 H, d, J=12.8), 1 .97 (1 H, d, J=10.0), 2.29 (3H,s), 2.41 (3H,s), 3.10-3.27 (3H, m), 3.92 (1 H, d, J=1 1 .6), 4.09 (1 H, d, J=1 1 .2), 4.29-4.42 (2H, m), 6.92 (1 H, s), 7.31 (2H, s), 7.36 (1 H, s), 7.43 (2H, d, J=8.4), 7.77 (2H, d, J=8.0), 8.60 (1 H, t, J=6.0).LCMS m/z (ES): 459, 460 [M+H]+.
Reference： [1]Patent: WO2011/131975,2011,A1 .Location in patent: Page/Page column 35-36
  • 81
  • 6-(2,3,4,5,6-pentafluorophenyl) 2-[[(6-carboxyhexyl)amino]carbonyl]-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-6-carboxylic acid [ No CAS ]
  • [ 138-37-4 ]
  • 7-[({6-[([4-(aminosulfonyl)phenyl]methyl}amino)carbonyl]-3a,4,7,7a-tetrahydro-4,7-methano-1Hinden-2-yl}carbonyl)amino]heptanoic acid [ No CAS ]
Reference： [1]Chemistry and biodiversity,2012,vol. 9,p. 1849 - 1866,18
  • 82
  • [ 138-37-4 ]
  • [ 1228647-59-3 ]
Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 510 - 520
  • 83
  • [ 138-37-4 ]
  • [ 1417996-78-1 ]
Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 510 - 520
  • 84
  • [ 138-37-4 ]
  • C30H38N6O9ReS(1+) [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 510 - 520
  • 85
  • [ 138-37-4 ]
  • C46H64N8O15ReS(1+) [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 510 - 520
  • 86
  • [ 1226869-60-8 ]
  • [ 138-37-4 ]
  • [ 1228647-88-8 ]
Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 510 - 520
  • 87
  • [ 1228647-94-6 ]
  • [ 138-37-4 ]
  • [ 1417889-94-1 ]
Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 510 - 520
  • 88
  • [ 138-37-4 ]
  • [ 1445903-47-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 4288 - 4295

Tags: 138-37-4 synthesis path| 138-37-4 SDS| 138-37-4 COA| 138-37-4 purity| 138-37-4 application| 138-37-4 NMR| 138-37-4 COA| 138-37-4 structure

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