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CAS No. : | 1293987-69-5 | MDL No. : | MFCD22190800 |
Formula : | C13H20BNO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YIIPTCFKYOTDME-UHFFFAOYSA-N |
M.W : | 297.18 | Pubchem ID : | 57416240 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.54 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 78.81 |
TPSA : | 73.01 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.79 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.87 |
Log Po/w (WLOGP) : | 1.97 |
Log Po/w (MLOGP) : | 0.36 |
Log Po/w (SILICOS-IT) : | 0.39 |
Consensus Log Po/w : | 0.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.88 |
Solubility : | 0.388 mg/ml ; 0.0013 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.02 |
Solubility : | 0.281 mg/ml ; 0.000944 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.35 |
Solubility : | 0.0132 mg/ml ; 0.0000446 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.19 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium acetate In dimethyl sulfoxide at 80℃; for 6h; | 29.2 3-Bromo-N-methylbenzenesulfonamide (1.6 g, 6.39 mmol) was dissolved in anhydrous DMSO (21 mL) and then potassium acetate (1.57 g, 15.99 mmol) and bis(pinacolato)diboron (1.63 g, 6.39 mmol) were added. After flowing nitrogen to the reaction mixture for 10 minutes, Pd(dppf)2Cl2 (522 mg, 0.64 mmol) was added. The reaction mixture was stirred at 80 °C for 6 hours, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (10% ethyl acetate/hexane) yielded the target compound (1.65 g, 86% yield). [0366] MS m/z: 298.52 [M+1]. |
69% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 6h; | |
69% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 6h; | 2-2 N-methyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzenesulfonamide (SMY-1283) 3-bromo-N-methylbenzenesulfonamide (SMY-1277; 730 mg, 2.9 mmol) obtained in Synthesis Example 2-1,Potassium acetate (AcOK; 716 mg, 7.3 mmol),Dichloro [1,1'-bis (diphenylphosphino) ferrocene] palladium.dichloromethane (PdCl 2 (dppf) · CH 2 Cl 2; 238 mg, 0.29 mmol),And bis pinacolate diboron (B 2 pin 2; 741 mg, 2.9 mmol)Of dimethylsulfoxide (DMSO; 10 mL)Was heated at 80 ° C. for 6 hours.After cooling to room temperature, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mL).Insolubles were filtered through celite. The filtrate was extracted with ethyl acetate (15 mL × 2).The combined organic layers were washed with water (20 mL × 1) and brine (20 mL × 1)Dry with Na 2 SO 4, filter and concentrate under vacuum.The obtained residue was purified by MPLC (hexane / ethyl acetate = 3: 1 to 15: 85)The target compound was obtained as a white solid (602 mg, 69%). |
65% | With sodium acetate In 1,4-dioxane at 80℃; Inert atmosphere; | PREPARATION 1/V-methyl-3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzenesulfonamideA mixture of 3-bromo-/V-methylbenzenesulfonamide (2.3 g, 9.0 mmol), 6/'s(pinacolato)diboron (2.5 g, 10.0 mmol), Pd(dppf)CI2 (0.725 g, 0.9 mmol), KOAc (2.6 g, 27 mmol), and dppf (0.700 g, 1 .26 mmol) in 1 ,4-dioxane was heated to 80 °C and stirred overnight under nitrogen. In the morning, the reaction mixture was filtered and concentrated in vacuo. The crude product was then purified via flash column chromatography (4:1 petroleum ether/EtOAc) to give A/-methyl-3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzenesulfonamide as a white solid (1 .7 g, 65%). |
With potassium acetate In N,N-dimethyl-formamide at 80℃; | 15.B The crude 15-B-2 (0.05Og, 0.20 mmol ), potassium acetate (0.059g O.Ommol), bis(pinacolato)diboron (0.046g, 0.18 mmol) and PdCl2(dppf) (0.016g 0.020mmol) were added to a round bottom flask. Dry DMF (3 ml) was then added, and the flask was flushed with nitrogen, then capped. The resultant mixture was stirred and placed into an 8O0C oil bath. The reaction was followed by LCMS. Upon consumption of starting material, the reaction mixture was extracted with ethyl acetate / water 3-4 times, then washed with brine twice. The resultant organic solution was dried over MgSO4 and concentrated to afford crude boronate ester 15-B-3 which was used directly for the Suzuki coupling without further purification, to provide Example 15-35. The Suzuki coupling was carried out using the standard conditions already described with the Boykin catalyst. | |
With potassium acetate In dimethyl sulfoxide at 80℃; for 6h; | 29.2 Step 2: N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 3-Bromo-N-methylbenzenesulfonamide (1.6 g, 6.39 mmol) was dissolved in anhydrous DMSO (21 mL) and then potassium acetate (1.57 g, 15.99 mmol) and bis(pinacolato)diboron (1.63 g, 6.39 mmol) were added. After flowing nitrogen to the reaction mixture for 10 minutes, Pd(dppf)2Cl2 (522 mg, 0.64 mmol) was added. The reaction mixture was stirred at 80° C. for 6 hours, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (10% ethyl acetate/hexane) yielded the target compound (1.65 g, 86% yield). MS m/z: 298.52 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 6 h / 80 °C | ||
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: potassium acetate / 1,1'-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride-chloroform adduct / dimethyl sulfoxide / 6 h / 80 °C | ||
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 °C 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 6 h / 80 °C |
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 °C 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 6 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 90℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene; methanol / 12 h / 70 °C / Inert atmosphere 2: potassium carbonate; thiophenol / 12 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene at 70℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.25% | In 1,4-dioxane at 20℃; for 15h; | 6II.1 Step 1: Synthesis of N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzenesulfonamide Methylamine, 40% w/w aq. soln. (2.71 g, 34.95 mmol, 3.02 mL, 40% purity) was added to a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonyl fluoride (2 g, 6.99 mmol) in dioxane (10 mL). Resulting mixture was stirred at 20°C for 15 hr. Then, volatiles were removed under reduced pressure and residue was diluted with water (15 ml). Resulting white precipitate was collected by filtration and dried, affording N-methyl-3-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (1.75 g, 5.89 mmol, 84.25% yield). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 1.32 (s, 12H), 2.62 (d, 3H), 4.48 (m, 1H), 7.51 (t, 1H), 7.91 (d, 1H), 7.96 (d, 1H), 8.25 (s, 1H). LCMS(ESI): [M]+ m/z: calcd 297.4; found 298.2; Rt = 1.323 min |
84.25% | In 1,4-dioxane at 20℃; for 15h; | 6II.1 Step 1: Synthesis of N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzenesulfonamide Methylamine, 40% w/w aq. soln. (2.71 g, 34.95 mmol, 3.02 mL, 40% purity) was added to a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonyl fluoride (2 g, 6.99 mmol) in dioxane (10 mL). Resulting mixture was stirred at 20°C for 15 hr. Then, volatiles were removed under reduced pressure and residue was diluted with water (15 ml). Resulting white precipitate was collected by filtration and dried, affording N-methyl-3-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (1.75 g, 5.89 mmol, 84.25% yield). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 1.32 (s, 12H), 2.62 (d, 3H), 4.48 (m, 1H), 7.51 (t, 1H), 7.91 (d, 1H), 7.96 (d, 1H), 8.25 (s, 1H). LCMS(ESI): [M]+ m/z: calcd 297.4; found 298.2; Rt = 1.323 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; water monomer at 90℃; for 15h; Inert atmosphere; | 6II.2 Step 2: Synthesis of tert-butyl 3-methyl-6-(3-(N-methylsulfamoyl)phenyl)-3,4-dihydropyridine- 1(2H)-carboxylate Sodium carbonate (1.56 g, 14.72 mmol, 616.74 μL) was added to a solution of N- methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (1.75 g, 5.89 mmol) and tert-butyl 3-methyl-6-(trifluoromethylsulfonyloxy)-3,4-dihydro-2H-pyridine-1-carboxylate (2.14 g, 6.18 mmol) in dioxane (17 mL) and water (6.5 mL). Reaction flask was evacuated and refilled with argon 3 times. Then, PdCl2dppf*DCM (192.36 mg, 235.55 μmol) was added under stream of argon. Resulting mixture was stirred at 90°C for 15 hr under inert atmosphere. Then, it was concentrated under reduced pressure and residue was extracted with ethyl acetate (50 ml). Obtained solution was filtered through a short pad of silica gel and evaporated under reduced pressure, affording tert-butyl 3-methyl-6-[3-(methylsulfamoyl)phenyl]-3,4-dihydro-2H- pyridine-1-carboxylate (3.98 g, crude). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 0.89 (d, 3H), 1.01 (s, 9H), 1.36 (m, 2H), 1.91 (m, 1H), 2.38 (d, 3H), 3.07 (m, 1H), 3.56 (m, 2H), 3.92 (m, 1H), 7.53 (m, 2H), 7.64 (m, 2H). LCMS(ESI): [M-Boc]+ m/z: calcd 266.4; found 267.2; Rt = 1.302 min | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; water monomer at 90℃; for 15h; Inert atmosphere; | 6II.2 Step 2: Synthesis of tert-butyl 3-methyl-6-(3-(N-methylsulfamoyl)phenyl)-3,4-dihydropyridine- 1(2H)-carboxylate Sodium carbonate (1.56 g, 14.72 mmol, 616.74 μL) was added to a solution of N- methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (1.75 g, 5.89 mmol) and tert-butyl 3-methyl-6-(trifluoromethylsulfonyloxy)-3,4-dihydro-2H-pyridine-1-carboxylate (2.14 g, 6.18 mmol) in dioxane (17 mL) and water (6.5 mL). Reaction flask was evacuated and refilled with argon 3 times. Then, PdCl2dppf*DCM (192.36 mg, 235.55 μmol) was added under stream of argon. Resulting mixture was stirred at 90°C for 15 hr under inert atmosphere. Then, it was concentrated under reduced pressure and residue was extracted with ethyl acetate (50 ml). Obtained solution was filtered through a short pad of silica gel and evaporated under reduced pressure, affording tert-butyl 3-methyl-6-[3-(methylsulfamoyl)phenyl]-3,4-dihydro-2H- pyridine-1-carboxylate (3.98 g, crude). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 0.89 (d, 3H), 1.01 (s, 9H), 1.36 (m, 2H), 1.91 (m, 1H), 2.38 (d, 3H), 3.07 (m, 1H), 3.56 (m, 2H), 3.92 (m, 1H), 7.53 (m, 2H), 7.64 (m, 2H). LCMS(ESI): [M-Boc]+ m/z: calcd 266.4; found 267.2; Rt = 1.302 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate / water monomer; 1,4-dioxane / 15 h / 90 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate / water monomer; 1,4-dioxane / 15 h / 90 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: methanol; sodium tetrahydridoborate / 1 h / 20 °C |
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