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[ CAS No. 874801-46-4 ] {[proInfo.proName]}

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Chemical Structure| 874801-46-4
Chemical Structure| 874801-46-4
Structure of 874801-46-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 874801-46-4 ]

CAS No. :874801-46-4 MDL No. :MFCD04973905
Formula : C6H3BrCl2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :FSNCFUWFJZQPTR-UHFFFAOYSA-N
M.W :289.96 Pubchem ID :2756864
Synonyms :

Calculated chemistry of [ 874801-46-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.24
TPSA : 42.52 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 3.44
Log Po/w (WLOGP) : 4.11
Log Po/w (MLOGP) : 2.85
Log Po/w (SILICOS-IT) : 2.69
Consensus Log Po/w : 3.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.11
Solubility : 0.0226 mg/ml ; 0.0000778 mol/l
Class : Moderately soluble
Log S (Ali) : -4.01
Solubility : 0.0281 mg/ml ; 0.0000969 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.4
Solubility : 0.0115 mg/ml ; 0.0000398 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.99

Safety of [ 874801-46-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:1759
Hazard Statements:H302-H312-H314-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 874801-46-4 ]

* 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 [ 874801-46-4 ]

[ 874801-46-4 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 874801-46-4 ]
  • [ 853308-08-4 ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: 4-bromo-3-chlorobenzene-1-sulfonyl chloride With triphenylphosphine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride; water In dichloromethane; N,N-dimethyl-formamide 1 4-Bromo-3-chloro-benzenesulfonyl chloride (3.78 g, 13.0 mmol) was dissolved in dichloromethane (40 ml) and DMF (1.0 ml) was added. The mixture was cooled to 0°C under argon and triphenylphosphine (10.26 g, 39.0 mmol) was added slowly, then the mixture was allowed to return to room temperature with stirring over 16 h. Hydrochloric acid (1 M, 75 ml) was added and the layers were separated. The organic layer was concentrated and the residue suspended in 1 M aqueous sodium hydroxide (75 ml) and filtered. The filtrate was extracted with Et2O (χ2), then neutralised (1 M HCl, 75 ml). The mixture was then extracted (Et2O χ3) and the combined organic layers were dried (Na2SO4) and concentrated to afford the title compound as a colourless oil (0.94 g, 32%). IH NMR (CDCl3400MHz) 3.49 (1 H, s), 7.02 (1 H, dd, J = 8.35, 2.24 Hz), 7.38 (1 H, d, J = 2.18 Hz), 7.45 (1 H, d, J = 8.35 Hz).
  • 2
  • [ 874801-46-4 ]
  • [ 1033006-33-5 ]
  • [ 1033006-31-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 20℃; for 0.25h; 3 1-(4-Bromo-3-chloro-benzenesulfonyl)-5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-indole; 1DE10335449, DE10335450, WO2005019169 [Show Image] 1.79 g of commercially available 4-bromo-benzenesulfonyl chloride were dissolved in 35 ml dichloromethane. Then 1.85 g 5-(4-trifluoromethylphenyl)-2,3-dihydro-1H-indole hydrochloride were added followed by 2.14 ml triethylamine. The mixture was stirred at room temperature for fifteen minutes. Then 100 ml of dichloromethane were added, the mixture washed with 40ml water and brine and then dried over MgSO4. The solvent was removed in vacuoto obtain 2.48g crude 1-(4-bromo-3-chlorobenzenesulfonyl)-5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-indole. This material was used without further purification. C21H14BrClF3NO2S (516.77), Rf(n-heptane: ethyl acetate = 1:1) = 0.61.
  • 3
  • [ 96-50-4 ]
  • [ 874801-46-4 ]
  • [ 1104807-01-3 ]
YieldReaction ConditionsOperation in experiment
58% With pyridine In dichloromethane at 0 - 20℃; for 16h; 4.1 Step 1. Preparation of 4-bromo-3-chloro-N-(thiazol-2-yl)benzenesulfonamide To a mixture of 2-aminothiazole (7.1 g, 70.7 mmol) in dichloromethane (190 mL) and pyridine (62 mL) was added 4-bromo-3-chlorobenzenesulfonyl chloride (20.5 g, 70.7 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. The mixture was concentrated under reduced pressure and the residue co-evaporated with toluene (2×100 mL). Trituration in methanol (50-100 mL) provided a solid which was filtered off. The solid was washed with methanol (50 mL) to provide the title compound as a beige powder (14.6 g, 58% yield): 1H NMR (300 MHz, DMSO-d6) δ12.07 (br s, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.90 (d, J=2.1 Hz, 1H), 7.65 (dd, J=8.4, 2.1 Hz, 1H), 7.32 (d, J=4.6 Hz, 1H), 6.90 (d, J 4.6 Hz, 1H); MS (ES+) m/z 352.9 (M+1), 354.9 (M+1).
With pyridine at 20℃; for 216h; 1 4-BROMO-3-CHLOROBENZENESULFONYL CHLORIDE (10.0 g, 0.0345 mol) and 2-AMINOTHIAZOLE (3.80 g, 0.0379 mol) were mixed in Pyridine (40 mL, 0.5 mol). The reaction was allowed to stir at room temperature for 9 days. The reaction was concentrated in vacuo to a total volume of approximately 40 mL. The residue was triturated with acetonitrile and the solid collected by filtration. The filtrate was concentrated in vacuo and the residue triturated with 1N HCl. The solid was collected by filtration and rinsed with acetonitrile then ethyl ether. The combined solid from steps 4 and 5 was dissolved in boiling acetonitrile and treated with activated carbon then filtered through a celite pad. The filtrate was reduced to its original volume by distillation. The mixture was cooled to room temperature. The crystals were collected by filtration and rised with ethyl ether. Vacuum drying gave 7.73 g of yellow solid
  • 5
  • [ 177908-37-1 ]
  • [ 874801-46-4 ]
  • 4-bromo-3-chloro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; Synthesis G 4-Bromo-3-chloro-/V-((1 r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamid To a solution of (1 r,4r)-4-amino-1 -methylcyclohexanol (1.2 g, 9.29 mmol) in dichloromethane (50 mL) was added diisopropylethylamine (2.99 g, 23.13 mmol) and the reaction mixture was cooled to 0C. 4-Bromo-3-chlorobenzenesulfonyl chloride (2.61 g, 9.0 mmol) was added and the reaction mixture was allowed to stir at room temperature for 3-4 hours. The reaction mixture was neutralized with 1 M hydrochloric acid and the compound was extracted into dichloromethane. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue obtained was washed with pentane, filtered and dried to afford the title compound (2.1 g, 59%). MS (ESI) m/z 380[M-H].
  • 6
  • [ 874801-46-4 ]
  • [ 1063733-41-4 ]
  • 4-bromo-3-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% To a mixture of <strong>[1063733-41-4]N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine</strong> (prepared according toW02010079443, 5.00 g, 19.90 mmol) in anhydrous THF (100 mL) was added a 1 M solution of lithium bis(trimethylsilyl)amide in THF (20.0 mL, 20.0 mmol) at 0 C and the reaction mixture was stirred for 1 h. The reaction mixture was cooled to -78 C and a solution of 4-bromo-3-chlorobenzenesulfonyl chloride (5.77 g, 19.90 nimol) in anhydrous THF (20 mL) was added. The reaction mixture was allowed to warm to ambient temperature, stirred for 2 h, and diluted with EtOAc (200 mL). The mixture was washed with saturated aqueous ammonium chloride (2 x 150 mL), brine (150 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo and trituration of the residue in MeOH (50 mL) provided the title compound as a colorless solid (9.00 g, 90% yield). 1H NMR (300 MHz, CDCl3) 68.22 (s, 1H), 7.66-7.63 (m, 2H), 7.47 (dd, J= 2.2, 8.5 Hz, 1H), 7.07 (d, J= 8.4 Hz, 1H), 6.34 (dd, J- 2.4, 8.4 Hz,1H), 6.27 (d, J- 2.4 Hz, 1H), 5.31 (s, 2H), 3.79 (s, 3H), 3.67 (s, 3H).
  • 7
  • [ 874801-46-4 ]
  • 3-chloro-N-(2,4-dimethoxybenzyl)-4-formyl-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / -78 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 2.2: 1 h
  • 8
  • [ 874801-46-4 ]
  • (R)-3-chloro-N-(2,4-dimethoxybenzyl)-4-((2-phenylpiperidin-1-yl)methyl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / -78 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 2.2: 1 h 3.1: tetrahydrofuran / 0.5 h / 20 °C 3.2: 18 h
  • 9
  • [ 874801-46-4 ]
  • (S)-3-chloro-4-((2-methylpyrrolidin-1-yl)methyl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / -78 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 2.2: 1 h 3.1: potassium acetate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 24 h 3.2: 0.67 h
  • 10
  • [ 874801-46-4 ]
  • (S)-3-chloro-4-((2-phenylpyrrolidin-1-yl)methyl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / -78 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 2.2: 1 h 3.1: potassium acetate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 24 h 3.2: 0.67 h
  • 11
  • [ 874801-46-4 ]
  • [ 1235406-42-4 ]
  • tert-butyl ((4-bromo-3-chlorophenyl)sulfonyl)(thiazol-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% To a solution of <strong>[1235406-42-4]tert-butyl thiazol-4-ylcarbamate</strong> (26.50 g, 132.33 mmol) in THF (300 mL) at -78 C, under nitrogen, was added 1 M solution of lithium bis(trimethylsilyl)amide in THF (185 mL, 185 mmol) dropwise. The mixture was warmed to 0 C and stirred for 1 h. The mixture was added dropwise a solution of 4-bromo-3-chlorobenzenesulfonyl chloride (49.88 g, 172.03 mmol) in THF (200 mL) at -78 C. The resulting mixture was stirred at 20 C for 3 h and then quenched with saturated aqueous sodium bicarbonate (100 mL) and water (300 mE). The mixture was extracted with EtOAc (3 x 300 mL) and the combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated in vacuo. The resdiue was triturated with MeOH (200 mL) to give the title compound as a colorless solid (35.00 g, 58% yield).MS (ES+) m/z: 476.9 (M + 23). 1H NMR (300 MHz, CDCl3) (5 8.82 (d, J = 2.0 Hz, 1H), 8.25 (a, J = 4.0 Hz, 1H), 7.95-7.89 (m, 1H), 7.87-7.83 (m, 1H), 7.58 (d, J = 4.0 Hz, 1H), 1.38 (s, 9H).
58% EXAMPLE 225 Synthesis of (f?)-4-((1 -benzyl-3-methylpyrrolidin-3-yl)amino)-3-chloro-//-(thiazol-4- yl)benzenesulfonamide formate To a mixture of te/f-butyl thiazol-4-ylcarbamate (26.5 g, 132.3 mmol) in anhydrous tetrahydrofuran (300 mL) was added a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (185.3 mL, 185.3 mmol) at -78 C. The reaction mixture was allowed to warm to 0 C and stirred for 1 h. After cooling the reaction mixture to -78 C, a solution of 4-bromo-3-chlorobenzenesulfonyl chloride (49.88 g, 172.0 mmol) in anhydrous tetrahydrofuran (200 mL) was added to it. The reaction mixture was allowed to warm to ambient temperature, stirred for 3 h, and then quenched by addition of saturated sodium bicarbonate solution (100 mL). The mixture was diluted with water (300 mL) and extracted with ethyl acetate (3 chi 300 mL). The combined organic phase was washed with brine (100 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo and trituration of the residue in methanol (200 mL) provided the title compound as a colorless solid (35.0 g, 58% yield): H NMR (400 MHz, CDCI3) 8.85-8.78 (d, J = 2.0 Hz, 1 H), 8.28-8.21 (d, J = 4.0 Hz, 1 H), 7.95-7.89 (m, 1 H), 7.87-7.83 (m, 1 H), 7.59-7.55 (d, J = 4.0 Hz, 1 H), 1.38 (s, 9H); MS (ES+) m/z 352.9 (M - 99), 354.9 (M - 99).
  • 12
  • [ 874801-46-4 ]
  • 4-bromo-3-chloro-N-(thiazol-4-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 0 °C 1.2: 3 h / -78 - 20 °C 2.1: hydrogenchloride / ethyl acetate / 72 h / 20 °C
  • 13
  • [ 874801-46-4 ]
  • (S)-3-chloro-4-(methyl(1-(2-phenylpropan-2-yl)pyrrolidin-3-yl)amino)-N-(thiazol-4-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 0 °C 1.2: 3 h / -78 - 20 °C 2.1: hydrogenchloride / ethyl acetate / 72 h / 20 °C 3.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 18 h / Inert atmosphere; Reflux
  • 14
  • [ 874801-46-4 ]
  • tert-butyl (R)-((4-((1-benzyl-3-methylpyrrolidin-3-yl)amino)-3-chlorophenyl)sulfonyl)(thiazol-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 0 °C 1.2: 3 h / -78 - 20 °C 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); caesium carbonate / toluene / 12 h / 100 °C
  • 15
  • [ 874801-46-4 ]
  • (R)-4-((1-benzyl-3-methylpyrrolidin-3-yl)amino)-3-chloro-N-(thiazol-4-yl)benzenesulfonamide formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 0 °C 1.2: 3 h / -78 - 20 °C 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); caesium carbonate / toluene / 12 h / 100 °C 3.1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C
  • 16
  • [ 874801-46-4 ]
  • 3-chloro-4-(methyl((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)amino)-N-(thiazol-4-yl)benzenesulfonamide 2,2,2-trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 0 °C 1.2: 3 h / -78 - 20 °C 2.1: hydrogenchloride / ethyl acetate / 72 h / 20 °C 3.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 18 h / Inert atmosphere; Reflux
  • 17
  • [ 874801-46-4 ]
  • (S)-(4,4-difluoropyrrolidin-2-yl)methanol [ No CAS ]
  • (S)-(1-((4-bromo-3-chlorophenyl)sulfonyl)-4,4-difluoropyrrolidin-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 20h; Intermediate 17: (S)-(1 -((4-bromo-3-chlorophenyl)sulfonyl)-4,4-difluoropyrrolidin-2-yl)methanol A solution of (S)-(4,4-difluoropyrrolidin-2-yl)methanol (120 mg, 0.69 mmol) in pyridine (3.5 ml) was treated with 4-bromo-3-chlorobenzene-1 -sulfonyl chloride (200 mg, 0.69 mmol) and was stirred at RT for 20 h. The reaction mixture was concentrated and the residue was purified by FCC to afford the title compound. (UPLC-MS, METHOD B) tR 1 .66 min; API-MS 390.0 [M+H]+.
With pyridine at 50℃; for 3h; Intermediate 2a: 4-bromo-N-((I s ,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3- methylbenzenesulfonamide. A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 °C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound. ;_ Intermediate I 8a: (S)-(1 -((4-bromo-3-chlorophenyl)sulfonyl)-4,4-difluoropyrrolidin-2- yl)methanol.The title compound was prepared in an analogous manner to 4-bromo-N-(3-hydroxy-3- (trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide (Intermediate 2a) using (S)-(4,4- difluoropyrrolidin-2-yl)methanol and 4-bromo-3-chlorobenzene-I-sulfonyl chloride to give thetitle compound. (UPLC-MS) tR 1 .56 mm; API-MS mlz: 390.0 [M+H].
  • 18
  • [ 19816-92-3 ]
  • [ 874801-46-4 ]
  • 5-(2-chloro-4-((3,3-dimethylazetidin-1-yl)sulfonyl)phenyl)-4-methyl-1H-indazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 1 h / 0 - 20 °C 2: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane; water / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation
  • 19
  • [ 19816-92-3 ]
  • [ 874801-46-4 ]
  • 1-((4-bromo-3-chlorophenyl)sulfonyl)-3,3-dimethylazetidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 0 - 20℃; for 1h; Intermediate 25: 1-((4-bromo-3-chlorophenyl)sulfonyl)-3,3-dimethylazetidine To a stirred solution of 4-bromo-3-chlorobenzene-1 -sulfonyl chloride (200 mg, 0.69 mmol) in pyridine (4 mL) was added 3,3- dimethylazetidine (59 mg, 0.69 mmol) at 0 °C. The reaction mixture was allowed to warm to rt and was stirred for additional 1 h. The reaction was quenched with 1 N HCI and extracted with ethyl acetate. The organic layer was washed with 1 N HCI and brine successively and was then dried over anhydrous sodium sulfate. The filtered organic layer was concentrated under vacuum to afford the title compound. (UPLC-MS, METHOD A) tR 1 .69 min. API-MS 337.9 [M+H]+.
  • 20
  • [ 874801-46-4 ]
  • 3-chloro-4-((1-(pyridin-2-yl)propyl)amino)-N-(thiazol-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 16 h / 0 - 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos / toluene / 72 h / 100 °C / Inert atmosphere
  • 21
  • [ 874801-46-4 ]
  • 3-chloro-4-(methyl(1-phenylpropyl)amino)-N-(thiazol-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 16 h / 0 - 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos / toluene / 18 h / 100 °C / Inert atmosphere
  • 22
  • [ 874801-46-4 ]
  • 3-chloro-4-((cyclopropyl(phenyl)methyl)amino)-N-(thiazol-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 16 h / 0 - 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos / toluene / 17 h / 100 °C / Inert atmosphere
  • 23
  • [ 874801-46-4 ]
  • [ 62-53-3 ]
  • 4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-phenylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pyridine / 2.5 h / 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); hexamethyldistannane / 1,4-dioxane / 24 h / 110 °C / Inert atmosphere 2.2: 2 h / 140 °C / Microwave irradiation
  • 24
  • [ 874801-46-4 ]
  • [ 62-53-3 ]
  • 4-bromo-3-methyl-N-phenylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h; Intermediate I a: 4-bromo-3-chloro-N-((1 s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide. A solution of 4-bromo-3-chlorobenzene-1-sulfonyl chloride (80 mg, 0.28 mmol) and (ls,3s)-3- amino-1-(trifluoromethyl)cyclobutan-1-ol hydrochloride (53 mg, 0.28 mmol) in DCM (2 mL) was stirred at 0 °C and DIPEA (0.15 mL, 0.83 mmol) was added. The reaction mixture was allowed to reach room temperature and stiirred for 2 h, then partitioned between EtOAc and an sat. aq. NaHCO3 solution. The aq. layer was extracted twice with EtOAc. The combined organic layers were washed wih brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (0 to 30% EtOAc in Cyclohexane) to give the title compound as a white solid. ; Intermediate 16a: 4-bromo-3-methyl-N-phenylbenzenesulfonamide.The title compound was prepared in an analogous manner to 4-bromo-3-chloro-N-((ls,3s)-3- hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide (Intermediate I a) using 4-bromo-3- methylbenzene-1-sulfonyl chloride and aniline to give the title compound as a colorless solid.(UPLC-MS) tR 1.15 mm; ESI-MS 328.0 [M+H].
  • 25
  • [ 874801-46-4 ]
  • [ 62-53-3 ]
  • 4-bromo-3-chloro-N-phenylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 2.5h; Intermediate 38c: 4-Bromo-3-chloro-N-phenylbenzenesulfonamide. To a solution of 4-bromo-3-chlorobenzene-1-sulfonyl chloride (1.00 g, 3.45 mmol) in anhydrous pyridine (6.9 mL) was added dropwise aniline (0.32 mL, 3.52 mmol). The reaction was stirredroom temperature for 2.5 h and then concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (0 to 100% EtOAc in Cyclohexane) to givetitle compound. (UPLC-MS) tR 1.14 mm; ESl-MS 346.6 [M+H].
  • 26
  • [ 874801-46-4 ]
  • 4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 0.5 h / 120 °C / Sealed tube; Microwave irradiation 3: hydrazine hydrate / water; ethanol / 2 h / 80 °C / Sealed tube
  • 27
  • [ 874801-46-4 ]
  • 3-chloro-4-(6-cyano-5-fluoropyridin-2-yl)-N-((1s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 0.5 h / 120 °C / Sealed tube; Microwave irradiation
  • 28
  • [ 372-19-0 ]
  • [ 874801-46-4 ]
  • 4-bromo-3-chloro-N-(3-fluorophenyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 17h; Intermediate 2a: 4-bromo-N-((I s ,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3- methylbenzenesulfonamide. A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 °C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound. :_Intermediate 40a: 4-bromo-3-chloro-N-(3-fluorophenyl)benzenesulfonamide.The title compound was prepared in an analogous manner to 4-bromo-N-(3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide (Intermediate 2a) using 4-bromo-3- 15 chlorobenzene-1-sulfonyl chloride and 3-fluoroaniline. The reaction mixture was stirred at RT for17 h to afford the title compound as a colorless solid. (UPLC-MS) tR 1.17 mm; ESI-MS362.0/364.0/366.0 [M+H].
  • 29
  • [ 874801-46-4 ]
  • [ 2106-04-9 ]
  • 4-bromo-3-chloro-N-(3-chloro-2-fluorophenyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 4.5h; Intermediate 2a: 4-bromo-N-((I s ,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3- methylbenzenesulfonamide. A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 °C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound;_Intermediate 52a: 4-bromo-3-chloro-N-(3-chloro-2-fluorophenyl)benzenesulfonamide.The title compound was prepared in an analogous manner to 4-bromo-N-(3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide (Intermediate 2a) using 4-bromo-3- chlorobenzene-1-sulfonyl chloride and 3-chloro-2-fluoroaniline. The reaction mixture was stirred at RT for 4.5 h. The title compound was obtained as a colorless solid. (UPLC-MS) tR 1 .22 mm; ESI-MS 395.9/397.9/399.9 [M-H].
  • 30
  • [ 874801-46-4 ]
  • [ 608-27-5 ]
  • 4-bromo-3-chloro-N-(2,3-dichlorophenyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 5.5h; Intermediate 2a: 4-bromo-N-((I s ,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3- methylbenzenesulfonamide. A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 °C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound. (UPLC-MS) tR 1.60 mm; API-MS 387.9 [M+H].
  • 31
  • [ 874801-46-4 ]
  • (3R)-pyrrolidinol [ No CAS ]
  • (R)-1-((4-bromo-3-chlorophenyl)sulfonyl)pyrrolidin-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 0℃; for 1h; Intermediate 2a: 4-bromo-N-((I s ,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3- methylbenzenesulfonamide. A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 °C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound. :_Intermediate 57a: (R)-1 -((4-bromo-3-chlorophenyl)sulfonyl)pyrrolidin-3-ol.The title compound was prepared in an analogous manner to 4-bromo-N-(3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide (Intermediate 2a) using 4-bromo-3-chlorobenzene-1-sulfonyl chloride and (R)-pyrrolidin-3-ol. The reaction mixture was stirred at0 °C for 60 mm. The title compound was obtained as a yellow solid. (UPLC-MS) tR 0.91 mm;ESI-MS 340.0/342.1 [M+H].
  • 32
  • [ 177908-37-1 ]
  • [ 874801-46-4 ]
  • 4-bromo-3-chloro-N-((1R,4R)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 0 - 20℃; for 7h; A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound. :_Intermediate 58a: 4-bromo-3-chloro-N-((1 R,4R)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide.The title compound was prepared in an analogous manner to 4-bromo-N-(3-hydroxy-3- (trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide (Intermediate 2a) using 4-bromo-3- chlorobenzene-1-sulfonyl chloride and (1 R,4R)-4-amino-1-methylcyclohexanol. The reaction mixture was stirred at 0 C for 30 mm and at RT for 6.5 h, then diluted with EtOAc. The organic layer was washed twice with a IN aq. NH4CI. The aq. layer was extracted twice with EtOAc. Thecombined organic layers were washed wih brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (0 to 40% EtOAc in Cyclohexane) to give the title compound as a white solid.(UPLC-MS) tR 0.94 mm; 380.0/382.1/384.0 [M-H].
  • 33
  • [ 874801-46-4 ]
  • [ 108-42-9 ]
  • 4-bromo-3-chloro-N-(3-chlorophenyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 4.5h; Intermediate 2a: 4-bromo-N-((I s ,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3- methylbenzenesulfonamide. A solution of (I s,3s)-3-amino-I -(trifluoromethyl)cyclobutan-I -ol hydrochloride (ActivateScientific, CAS Nr. 1408075-93-3) (249 mg, 1.30 mmol) in pyridine (6.5 ml) was treated with 4-bromo-3-methylbenzenesulfonyl chloride (Sigma-Aldrich, CAS Nr. 72256-93-0) (350 mg, 1 .30 mmol) and stirred at 50 °C for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting product was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to afford the title compound. (UPLC-MS) tR 1.60 mm; API-MS 387.9 [M+H].;_Intermediate 90a: 4-bromo-3-chloro-N-(3-chlorophenyl)benzenesulfonamide. The title compound was prepared in an analogous manner to 4-bromo-N-(3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide (Intermediate 2a) using 4-bromo-3- chlorobenzene-1-sulfonyl chloride and 3-chloroaniline I. The reaction mixture was stirred at RT for 4.5 h. The title compound was obtained as a colorless solid. (UPLC-MS) tR 1 .23 mm; ESI-MS 377.9/379.9/381 .9 [M-H].
  • 34
  • [ 874801-46-4 ]
  • (1s,3s)-3-amino-1-(trifluoromethyl)cyclobutan-1-ol hydrochloride [ No CAS ]
  • 4-bromo-3-chloro-N-((1s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h; Intermediate I a: 4-bromo-3-chloro-N-((1 s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide. A solution of 4-bromo-3-chlorobenzene-1-sulfonyl chloride (80 mg, 0.28 mmol) and (ls,3s)-3- amino-1-(trifluoromethyl)cyclobutan-1-ol hydrochloride (53 mg, 0.28 mmol) in DCM (2 mL) was stirred at 0 °C and DIPEA (0.15 mL, 0.83 mmol) was added. The reaction mixture was allowed to reach room temperature and stiirred for 2 h, then partitioned between EtOAc and an sat. aq. NaHCO3 solution. The aq. layer was extracted twice with EtOAc. The combined organic layers were washed wih brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (0 to 30% EtOAc in Cyclohexane) to give the title compound as a white solid. (UPLC-MS) tR 1 .07 mm; ESIMS 408.0 [M-H].
  • 35
  • [ 874801-46-4 ]
  • 3-chloro-4-((1-(1-methyl-1H-pyrazol-4-yl)ethyl)amino)-N-(thiazol-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 16 h / 0 - 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos / toluene / 72 h / 100 °C / Inert atmosphere
  • 38
  • [ 874801-46-4 ]
  • 2-chloro-4-(ethylsulfonyl)-2'-fluoro-5'-(4-methoxybenzyloxy)biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 2: sodium acetate / ethanol / 18 h / Reflux 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 110 °C
  • 39
  • [ 874801-46-4 ]
  • 2'-chloro-4'-(ethylsulfonyl)-6-fluorobiphenyl-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 2: sodium acetate / ethanol / 18 h / Reflux 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 110 °C 4: trifluoroacetic acid / dichloromethane / 20 °C
  • 40
  • [ 874801-46-4 ]
  • 2'-chloro-4'-(ethylsulfonyl)-6-fluorobiphenyl-3-yl trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 2: sodium acetate / ethanol / 18 h / Reflux 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 110 °C 4: trifluoroacetic acid / dichloromethane / 20 °C 5: 2,6-dimethylpyridine / dichloromethane
  • 41
  • [ 874801-46-4 ]
  • 2-(2'-chloro-4'-(ethylsulfonyl)-6-fluorobiphenyl-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 2: sodium acetate / ethanol / 18 h / Reflux 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 110 °C 4: trifluoroacetic acid / dichloromethane / 20 °C 5: 2,6-dimethylpyridine / dichloromethane 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 110 °C
  • 42
  • [ 874801-46-4 ]
  • 4-(2'-chloro-4'-(ethylsulfonyl)-6-fluorobiphenyl-3-yl)-7-ethyl-7H-imidazo[4,5-c]pyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 2: sodium acetate / ethanol / 18 h / Reflux 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 110 °C 4: trifluoroacetic acid / dichloromethane / 20 °C 5: 2,6-dimethylpyridine / dichloromethane 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 110 °C 7: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 1 h / 110 °C
  • 43
  • [ 116797-02-5 ]
  • [ 874801-46-4 ]
  • 1'-((4-bromo-3-chlorophenyl)sulfonyl)-4-methyl-1,4'-bipiperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
  • 44
  • [ 874801-46-4 ]
  • [ 1032507-45-1 ]
YieldReaction ConditionsOperation in experiment
88% With ammonia In acetonitrile at 20℃; for 0.166667h; 52a.1 Step 1: 4-bromo-3-chlorobenzenesulfonamide (2) To an ice cooled solution of 4-bromo-3-chlorobenzenesulfonyl chloride (1, 0.450 g, 1.55 mmol) in acetonitrile (7.76 mL) was added 25 % ammonia solution (0.602 mL, 3.88 mmol) dropwise. The mixture was stirred for 10 min at RT, diluted with water and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, filtered and the solvent removed under reduced pressure to yield 4-bromo-3-chlorobenzenesulfonamide (0.370 g, 1,37 mmol, 88% yield). (0867) Analytical data: (0868) 1H NMR (200 MHz, DMSO) δ 8.01 (d, J = 8.1 Hz, 2H), 7.89- 7.47 (m, 3H); (0869) 13C NMR (50 MHz, DMSO) δ 144.9, 134.8, 133.8, 127.3, 125.8, 125.5; (0870) MS: [M-1]- = 267.7.
88% With ammonia In acetonitrile at 20℃; for 0.166667h; 4-Bromo-3-chlorobenzenesulfonamide (R7). To anice cooled solution of 4-bromo-3-chlorobenzenesulfonyl chloride (0.45 g, 1.55mmol) in acetonitrile (10 mL) was added 25 % ammonia solution (0.60 mL, 3.9mmol) dropwise. The mixture was stirred for 10 min at RT, dilutedwith water and extracted with EtOAc. The extract was washed with brine, driedover sodium sulfate, filtered and the solvent removed under reduced pressure.Yield: 0.37 g (88%).
With ammonia In methanol at 20℃; for 10h;
  • 45
  • [ 874801-46-4 ]
  • 3-chloro-4-[3-[2,6-difluoro-3-(propylsulfonylamino)benzoyl]-1H-pyrazolo[3,4-b]pyridin-5-yl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonia / acetonitrile / 0.17 h / 20 °C 2: potassium carbonate / 1,4-dioxane; water / 1 h / 55 °C / Inert atmosphere
  • 46
  • [ 874801-46-4 ]
  • [ 124-40-3 ]
  • 4-bromo-3-chloro-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In tetrahydrofuran at 20℃; for 3h; 85.V-4 Intermediate V-4: 4-bromo-3-chloro-N,N-dimethylbenzenesulfonamide 4-bromo-3 -chlorobenzene- l-sulfonyl chloride (200 mg, 0.690 mmol) was dissolved in a solution of dimethylamine (2 M in THF) (2 mL, 4.00 mmol) and stirred at rt for 3 h. The mixture was diluted with DCM (20 mL) and extracted with water (3 x 10 mL) and brine (10 mL). The organic phase was dried by passing through a hydrophobic frit then concentrated in vacuo. The crude product was purified by chromatography on silica gel (12 g cartridge, 0- 50% EtO Ac/isohexane) to afford 4-bromo-3-chloro-N,N-dimethylbenzenesulfonamide (182 mg, 0.610 mmol, 88 % yield) as a colourless crystalline solid. Analytical data: Rl 1.44 min (Method 3); no mass observed.
  • 47
  • [ 874801-46-4 ]
  • 4-bromo-3-chlorobenzenesulfonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water at 100℃; for 16h; P33 4-Bromo-3-chlorobenzenesulfonic acid (P31) A solution of 4-bromo-3-chlorobenzenesulfonyl chloride (576 mg, 2.00 mmol) in H20 (30 mL) was stirred at 100°C for 16 h and concentrated to give compound P33 as a white solid
  • 48
  • [ 874801-46-4 ]
  • tert-butyl ((3-chloro-4-fluorophenyl)sulfonyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonia / methanol / 10 h / 20 °C 2: dmap; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 49
  • [ 874801-46-4 ]
  • 3-chloro-4-((3,4-difluorophenyl)amino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ammonia / methanol / 10 h / 20 °C 2: dmap; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 50
  • [ 874801-46-4 ]
  • C17H17ClF2N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ammonia / methanol / 10 h / 20 °C 2: dmap; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
  • 51
  • [ 874801-46-4 ]
  • C17H20F2N4O2S*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ammonia / methanol / 10 h / 20 °C 2: dmap; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 5: caesium carbonate; palladium diacetate; XPhos / tetrahydrofuran; water / 12 h / 100 °C / Inert atmosphere 6: dichloromethane / 2 h / 20 °C
  • 52
  • [ 874801-46-4 ]
  • C22H28F2N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: ammonia / methanol / 10 h / 20 °C 2: dmap; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 5: caesium carbonate; palladium diacetate; XPhos / tetrahydrofuran; water / 12 h / 100 °C / Inert atmosphere
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Chlorides

Chemical Structure| 1208076-53-2

[ 1208076-53-2 ]

4-Bromo-3,5-dichlorobenzene-1-sulfonyl chloride

Similarity: 0.98

Chemical Structure| 195201-10-6

[ 195201-10-6 ]

3-Bromo-4-chlorobenzene-1-sulfonyl chloride

Similarity: 0.96

Chemical Structure| 1049026-36-9

[ 1049026-36-9 ]

3-Bromo-5-chlorobenzenesulfonyl chloride

Similarity: 0.90

Chemical Structure| 1208076-85-0

[ 1208076-85-0 ]

4-Bromo-2,3-dichlorobenzene-1-sulfonyl chloride

Similarity: 0.88

Chemical Structure| 1349708-80-0

[ 1349708-80-0 ]

3-Bromo-2,4-dichlorobenzene-1-sulfonyl chloride

Similarity: 0.87