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Chemistry
Organometallic Reagents
Organoboron
(3-(N-Cyclopropylsulfamoyl)phenyl)boronic acid
Chemistry
Organometallic Reagents
Organic Building Blocks
Organoboron
Aryls Amines Sulfamides Benzene Compounds

[ CAS No. 913835-28-6 ]

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Chemical Structure| 913835-28-6
Chemical Structure| 913835-28-6
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Product Details of [ 913835-28-6 ]

CAS No. :913835-28-6 MDL No. :MFCD08436035
Formula : C9H12BNO4S Boiling Point : 484.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :241.07 g/mol Pubchem ID :-
Synonyms :

Safety of [ 913835-28-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P304+P340-P302+P352-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 913835-28-6 ]

  • Downstream synthetic route of [ 913835-28-6 ]

[ 913835-28-6 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 875639-69-3 ]
  • [ 913835-28-6 ]
  • [ 1188409-83-7 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,2-dimethoxyethane for 1h; Reflux; 2 A suspension of 2-Amino-5-bromo-N-methoxy-N-methyl-nicotinamide (0.2 g, 0.77 mmol), N-cyclopropyl 3-boronobenzenesulfonamide (0.2 g, 0.84 mmol), Pd(dppf)Cl2.DCM (0.063 g, 0.077 mmol) in 2M Na2CO3 (1 ml) and DME (3 ml) is heated at reflux for 1 hour. The crude reaction mixture is subjected to column chromatography (Isolute C18, 0-100% MeCN in water -0.1% TFA). All the acetonitrile is removed in vacuo, and the aqueous solution remaining is adjusted to basic pH using NaHCO3. The product is extracted into DCM, and dried (MgSO4). Concentration and drying in vacuo at 40° C. yields the title compound. [M+H]+ 726
Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2009/239847, 2009, A1 Location in patent: Page/Page column 45
  • 2
  • [ 913835-28-6 ]
  • [ 1580454-37-0 ]
  • [ 1580453-54-8 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere;
Reference： [1]Le Manach, Claire; Gonzàlez Cabrera, Diego; Douelle, Frederic; Nchinda, Aloysius T.; Younis, Yassir; Taylor, Dale; Wiesner, Lubbe; White, Karen L.; Ryan, Eileen; March, Corinne; Duffy, Sandra; Avery, Vicky M.; Waterson, David; Witty, Michael J.; Wittlin, Sergio; Charman, Susan A.; Street, Leslie J.; Chibale, Kelly [Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2789 - 2798]
  • 3
  • [ 195457-61-5 ]
  • [ 913835-28-6 ]
  • 3-(4-((3-chloro-4-fluorophenyl)amino)quinazolin-6-yl)-N-cyclopropylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With potassium carbonate In 1,4-dioxane at 100 - 120℃; for 0.45h; Inert atmosphere; Sealed tube; Microwave irradiation; 6 3-(4-((3-chloro-4-fluorophenyl)amino)iuinazolin-6-yl)-N-cyclopropylbenzenesulfonamide,MOL-214 A mixture consisting of 6-bromo-N-(3-chlorophenyl)quinazolin-4-amine - HC1 (100 mg 0.26 mmol), (3-(N-cyclopropylsulfamoyl)phenyl)boronic acid (94 mg, 0.39 mmol) and 1 .4M K2C03 (1.1 mL) in 3 ml. of 1 ,4-dioxane was degassed (vacuum/nitrogen, 3 times). To the reaction mixture was added SiliCat DPP-Pd (50 mg, 0.26 mmol/g loading). The reaction mixture was sealed and heated at 100 °C for 12 minutes in a Biotage Emrys Optimizer microwave. To the reaction mixture was added additional 2-chloro-5-(4,4,5 ,5-tetramethyl- 1 ,3,2-dioxaborolan-2- yl)aniline (40 mg, 0.16 mmol) and SiliCat DPP-Pd (30 mg). The reaction mixture was heated again at 120 °C for 15 minutes and cooled. The aqueous phase was removed and the remainingorganic phase was filtered through a glass frit. The solids were washed with methanol. The filtrate was concentrated under reduced pressure. The white solid residue was applied to a 40 g silica column using the dry loading method and eluted with a gradient of 4:6 ethyl acetateheptane to 100% ethyl acetate to give 20 mg (16%, purity 96%) of the title compound as a pale yellow solid; MS (ES-API+) m/z 469.0 (M+1), 471.0 (Cl isotope); ‘H NMR (400 MHz, DMSO10 d6)ö 10.13 (s, 1H), 8.87 (s, 1H), 8.67 (s, 1H), 8.14-8.27 (m, 4H), 8.01 (d,J=2.65 Hz, 1H), 7.95 (d, J8.69 Hz, 1H), 7.87-7.92 (m, 1H), 7.79-7.87 (m, 2H), 7.49 (t, J=9.06 Hz, 1H), 2.17 (dt,J3.34, 6.75 Hz, 1H), 0.37-0.54 (m, 4H).
Reference： [1]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2016/100347, 2016, A2 Location in patent: Page/Page column 79; 80
  • 4
  • [ 913835-28-6 ]
  • 3-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(1H-tetrazol-5-yl)phenyl]-L-phenylalaninamide [ No CAS ]
  • tert-butyl [(trans-4-[(2S)-3-[3'-(cyclopropylsulphamoyl)biphenyl-3-yl]-1-oxo-1-[4-(1H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; dimethyl sulfoxide at 110℃; for 1.5h; Microwave irradiation; 42A Example 42A tert-Butyl [(trans-4-[(2S)-3-[3'-(cyclopropylsulphamoyl)biphenyl-3-yl]-1-oxo-1-[4-(1H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate Example 42A tert-Butyl [(trans-4-[(2S)-3-[3'-(cyclopropylsulphamoyl)biphenyl-3-yl]-1-oxo-1-[4-(1H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate 3-Bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(1H-tetrazol-5-yl)phenyl]-L-phenylalaninamide (150 mg, 0.24 mmol) and [3-(cyclopropylsulphamoyl)phenyl]boronic acid (88 mg, 0.36 mmol) were dissolved in dimethyl sulphoxide (2 ml), and tetrakis(triphenylphosphine)palladium(0) (28 mg, 24 μmol), sodium carbonate (76 mg, 0.72 mmol) and water (0.36 ml, 20 mmol) were added. The reaction mixture was stirred at 110° C. in a microwave (Biotage Initiator) for 90 min, cooled, filtered and purified by chromatography via HPLC (Method 10). This gave 25 mg (18% of theory) of the title compound. LC-MS (Method 4): Rt=1.23 min; MS (ESIpos): m/z=743.4 [M+H]+.
Reference： [1]Current Patent Assignee: BAYER AG - US2016/244437, 2016, A1 Location in patent: Paragraph 0908; 0909; 0910
  • 5
  • [ 442129-37-5 ]
  • [ 913835-28-6 ]
  • (7R)-N-{6-[3-(cyclopropylsulfamoyl)phenyl]-5-methylpyridin-2-yl}-2,2-difluoro-7-methyl-6,7-dihydro-2H-furo[2,3-f][1,3]benzodioxole-7-carboxamide [ No CAS ]
Reference： [1]Patent: US2017/15675,2017,A1
  • 6
  • [ 442129-37-5 ]
  • [ 913835-28-6 ]
  • 3-(6-amino-3-methylpyridin-2-yl)-N-cyclopropylbenzene-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; Example 124A 3-(6-amino-3-methylpyridin-2-yl)-N-cyclopropylbenzene-1-sulfonamide (3-(N-cyclopropylsulfamoyl)phenyl)boronic acid (CAS [913835-28-6], 0.250 g, 1.037 mmol), <strong>[442129-37-5]6-chloro-5-methylpyridin-2-amine</strong> (0.158 g, 1.110 mmol), PdCl2dppf (0.053 g, 0.073 mmol), and potassium carbonate (0.330 g, 2.385 mmol) in dimethoxyethane (2.8 mL) and water (1.4 mL) were heated at 80 C. overnight. The mixture was then diluted with ethyl acetate (20 mL) and washed with water (3*5 mL) and brine (5 mL). It was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography, eluting with 20 to 100% ethyl acetate-heptanes, to afford the title compound was obtained as a gold residue (0.166 g, 53%). 1H NMR (400 MHz, DMSO-d6) delta 7.97-7.85 (m, 2H), 7.85-7.59 (m, 3H), 7.34 (d, J=8.3 Hz, 1H), 6.44 (d, J=8.3 Hz, 1H), 5.83 (s, 2H), 2.13 (s, 3H), 2.08 (m, 1H), 0.55-0.32 (m, 4H). MS (DCI+) m/z 304.0 (M+H).
Reference： [1]Patent: US2017/15675,2017,A1 .Location in patent: Paragraph 1221
  • 7
  • [ 913835-28-6 ]
  • 3-[1-(benzenesulfonyl)-5-bromo-pyrrolo[2,3-b]pyridin-2-yl]prop-2-yn-1-ol [ No CAS ]
  • 3-[1-(benzenesulfonyl)-2-(3-hydroxyprop-1-ynyl)pyrrolo[2,3-b]pyridin-5-yl]-N-cyclopropyl-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; acetonitrile at 130℃; for 0.5h; Microwave irradiation; 5.2 Step 2-Preparation of 3-[1-(benzenesulfonyl)-2-(3-hydroxyprop-1-ynyl)pyrrolo[2,3-b]pyridin-5-yl]-N-cyclopropyl-benzenesulfonamide, 36 Step 2-Preparation of 3-[1-(benzenesulfonyl)-2-(3-hydroxyprop-1-ynyl)pyrrolo[2,3-b]pyridin-5-yl]-N-cyclopropyl-benzenesulfonamide, 36 A mixture of 3-[1-(benzenesulfonyl)-5-bromo-pyrrolo[2,3-b]pyridin-2-yl]prop-2-yn-1-ol 35 (70 mg, 0.18 mmol), [3-(cyclopropylsulfamoyl)phenyl]boronic acid (65 mg, 0.27 mmol), aqueous potassium carbonate (0.17 ml, 2.5 M) and [1,1'-Bis(diphenylphosphino) ferrocene]dichloropalladium(II) dichloromethane complex (0.020 g, 0.025 mmol) in acetonitrile was allowed to stir at 130° C. for 30 minutes with microwave irradiation. The reaction mixture was filtered through Celite. The filtrate pH was adjusted with aqueous ammonium chloride and then was extracted with ethyl acetate. The organic layer was collected and washed with brine, then dried over magnesium sulfate. After removal of drying agent and solvent, the residue was dried under vacuum to provide 3-[1-(benzenesulfonyl)-2-(3-hydroxyprop-1-ynyl)pyrrolo[2,3-b]pyridin-5-yl]-N-cyclopropyl-benzenesulfonamide 36.
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2017/158690, 2017, A1 Location in patent: Paragraph 0541; 0543
  • 8
  • [ 913835-28-6 ]
  • C11H7BrF2N2O [ No CAS ]
  • 3-(6-amino-5-(3,5-difluoro-4-hydroxyphenyl)pyridin-3-yl)-N-cyclopropylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In ethanol; water at 85℃; for 1h; Inert atmosphere; Microwave irradiation;
Reference： [1]Serafim, Ricardo A. M.; De Souza Gama, Fernando H.; Dutra, Luiz A.; Dos Reis, Caio V.; Vasconcelos, Stanley N. S.; Da Silva Santiago, André; Takarada, Jéssica E.; Di Pillo, Fúlvia; Azevedo, Hatylas; Mascarello, Alessandra; Elkins, Jonathan M.; Massirer, Katlin B.; Gileadi, Opher; Guimarães, Cristiano R. W.; Couñago, Rafael M. [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 9, p. 1266 - 1271]
  • 9
  • [ 913835-28-6 ]
  • 4-(4-bromo-2-(2-methyl-4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl)pyridine [ No CAS ]
  • N-cyclopropyl-3-(2-(2-methyl-4-(methylsulfonyl)phenyl)-5-(pyridin-4-yl)-1H-imidazol-4-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: (3-(N-cyclopropylsulfamoyl)phenyl)boronic acid; 4-(4-bromo-2-(2-methyl-4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl)pyridine With (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; palladium diacetate In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With potassium carbonate In water; 1,2-dichloro-ethane at 20 - 80℃; for 18.0833h; Inert atmosphere;
Reference： [1]De Toledo, Ian; Grigolo, Thiago A.; Bennett, James M.; Elkins, Jonathan M.; Pilli, Ronaldo A. [Journal of Organic Chemistry, 2019, vol. 84, # 21, p. 14187 - 14201]

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