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CAS No. : | 913835-28-6 | MDL No. : | MFCD08436035 |
Formula : | C9H12BNO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WIZSPBQIRRAOMO-UHFFFAOYSA-N |
M.W : | 241.07 | Pubchem ID : | 44119335 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 59.66 |
TPSA : | 95.01 Ų |
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) : | -7.52 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.35 |
Log Po/w (WLOGP) : | -0.17 |
Log Po/w (MLOGP) : | -0.79 |
Log Po/w (SILICOS-IT) : | -1.68 |
Consensus Log Po/w : | -0.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.57 |
Solubility : | 6.51 mg/ml ; 0.027 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.91 |
Solubility : | 2.97 mg/ml ; 0.0123 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.87 |
Solubility : | 3.24 mg/ml ; 0.0135 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.46 |
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: |
* 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 |
---|---|---|
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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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]+. |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
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