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CAS No. : | 850589-31-0 | MDL No. : | MFCD07363752 |
Formula : | C9H14BNO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PMNOLRUYDNBEFQ-UHFFFAOYSA-N |
M.W : | 243.09 | Pubchem ID : | 44119552 |
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 : | 61.78 |
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) : | -7.36 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.59 |
Log Po/w (WLOGP) : | 0.13 |
Log Po/w (MLOGP) : | -0.4 |
Log Po/w (SILICOS-IT) : | -1.66 |
Consensus Log Po/w : | -0.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.73 |
Solubility : | 4.5 mg/ml ; 0.0185 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.16 |
Solubility : | 1.69 mg/ml ; 0.00694 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.1 |
Solubility : | 1.95 mg/ml ; 0.00804 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.37 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-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 bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 90℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 2h; Reflux; Inert atmosphere; | 37 [6-Chloro-4-(4-isopropylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester A stirred solution of (6-chloro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (0.20 g, 0.50 mmol) in dimethoxyethane (10 mL) was purged with argon for 5 minutes at room temperature. Triphenylphosphine (0.030 g, 0.11 mmol), palladium (II) acetate (0.013 g, 0.055 mmol), 4-(N-isopropylylsulfamoyl)phenylboronic acid (0.165 g, 0.68 mmol) and a 2 M aqueous solution of sodium carbonate (1.0 mL, 2.0 mmol) were added simultaneously to the reaction mixture at room temperature under argon. The reaction mixture was refluxed for 2 hours and then cooled to room temperature. Water was added and the mixture was extracted twice with ethyl acetate. The collected organic extracts were washed with water and then brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product, which was finally purified using flash chromatography (Biotage, 5-10% ethyl acetate-hexane) to afford [6-chloro-4-(4-isopropylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (0.03 g, 13%) as a solid. MS calcd. for C23H23ClNO4S [(M-H)-] 444, obsd. 444.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 2h; Reflux; Inert atmosphere; | 50 [6-Fluoro-4-(4-isopropylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester A stirred solution of (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (0.20 g, 0.52 mmol) in dimethoxyethane (10 mL) for 5 minutes at room temperature. Triphenylphosphine (0.031 g, 0.12 mmol), palladium (II) acetate (0.013 g, 0.06 mmol), 4-(N-isopropylylsulfamoyl)phenylboronic acid (0.173 g, 0.71 mmol) and a 2 M aqueous solution of sodium carbonate (1.0 mL, 2.0 mmol) were added simultaneously to the reaction mixture at room temperature under argon. The reaction mixture was refluxed for 2 hours and then cooled to room temperature. Water was added and the mixture was extracted twice with ethyl acetate. The collected organic extracts were washed with water and then brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product, which was finally purified using flash chromatography (Biotage, 5-10% ethyl acetate-hexane) to afford [6-fluoro-4-(4-isopropylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (0.161 g, 72%) as a solid. MS calcd. for C23H23FNO4S [(M-H)-] 428, obsd. 428.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With tetrakis(triphenylphosphine) palladium(0) In water at 20 - 150℃; for 0.266667h; Microwave irradiation; | 4-(1-(trans-4-Hydroxycyclohexyl)-6-(butylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-methylbenzenesulfonamide (10) and 4-(1-(cis-4-hydroxycyclohexyl)-6-(butylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-methylbenzenesulfonamide (11) General procedure: A mixture of 4 (0.054g, 0.20mmol), K2CO3 (0.11g, 0.8mmol), DMF (2.0mL), and 4-chlorocyclohexanol (0.081g, 0.6mmol) in a 10mL microwave tube was heated under microwave irradiation at 200°C for 30min. After cooling to room temperature, (4-(N-methylsulfamoyl)phenyl)boronic acid (0.065g, 0.30mmol), Pd(PPh3)4 (0.023g, 0.020mmol), and H2O (1.0mL) were added sequentially. The resulting mixture was stirred at room temperature for 1.0min and then heated under microwave irradiation at 150°C for 15min. After cooling to room temperature, the mixture was quenched with H2O and extracted with EtOAc (3×). The combined organic layer was dried (Na2SO4) and concentrated. The residue was purified by prep-HPLC to provide the title compounds 10 (0.011g, 13% over 3 steps) and 11 (0.020g, 23% over 3 steps) as white solids. 1H NMR (400MHz, CDCl3) δ 8.78 (s, 1H), 7.92 (d, J=8.4Hz, 2H), 7.82 (d, J=8.3Hz, 2H), 4.51 (s, 1H), 3.64 (s, 1H), 3.37 (t, J=7.0Hz, 2H), 2.50 (s, 3H), 2.17-1.86 (m, 6H), 1.61-1.29 (m, 6H), 0.87 (t, J=7.3Hz, 3H); LC-MS: >97% purity, tR=5.402min; HRMS (TOF, ESI+) m/z: [M+H]+ calculated for C22H31N6O3S, 459.2178; found 459.2155. Compound 11: 1H NMR (400MHz, CDCl3+CD3OD) δ 8.82 (s, 1H), 7.95 (dd, J=8.2, 6.2Hz, 2H), 7.84 (dd, J=8.5, 1.8Hz, 2H), 4.66-4.48 (m, 1H), 3.44-3.33 (m, 3H), 2.53 (s, 3H), 2.46-2.32 (m, 1H), 1.99-1.81 (m, 3H), 1.79-1.61 (m, 3H), 1.55 (dt, J=14.8, 7.4Hz, 2H), 1.36 (td, J=14.8, 7.4Hz, 3H), 0.88 (t, J=7.3Hz, 3H); LC-MS: >97% purity, tR=5.590min; MS m/z 459.2 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
160 mg | With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium carbonate In 1,2-dimethoxyethane; water at 140℃; for 1h; Microwave irradiation; | 1.3 (3) Synthesis of (R)-4-(3-(4-fluorophenyl)-6-methyl- 5,6,8,9-tetrahydroimidazo[1 ,5-d][1,4]oxazepin-1 -yl)N-isopropylbenzenesulfonamide (3) Synthesis of (R)-4-(3-(4-fluorophenyl)-6-methyl-5,6,8,9-tetrahydroimidazo[1,5-d][1,4]oxazepin-1-yl)-N-isopropylbenzenesulfonamide A DME solution (7 mL) of the compound obtained in Example 1-(2) (165 mg, 0.507 mmol), 4-(N-isopropylsulfamoyl)phenylboronic acid (173 mg, 0.710 mmol), (A-taPhos)2PdCl2 (35.9 mg, 0.051 mmol), and a 1 N aqueous sodium carbonate solution (2 mL) was stirred under microwave irradiation at 140° C. for 60 minutes. The reaction mixture was purified by NH silica gel column chromatography (n-heptane/ethyl acetate to ethyl acetate/methanol) to obtain the title compound (160 mg, 0.361 mmol). 1H-NMR (500 MHz, CDCl3) δ (ppm): 1.09 (d, J=6.3 Hz, 6H), 1.26 (d, J=6.3 Hz, 3H), 3.15-3.24 (m, 1H), 3.29-3.35 (m, 1H), 3.48 (dq, J=13.7, 6.6 Hz, 1H), 3.68 (t, J=11.2 Hz, 1H), 3.75-3.83 (m, 1H), 3.99 (dd, J=14.6, 8.3 Hz, 1H), 4.18-4.28 (m, 3H), 7.18 (t, J=8.8 Hz, 2H), 7.51 (dd, J=8.5, 5.1 Hz, 2H), 7.74 (d, J=8.8 Hz, 2H), 7.89 (d, J=8.8 Hz, 2H). ESI-MS m/z 444[M+H]+ |