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CAS No. : | 100859-88-9 | MDL No. : | MFCD12407811 |
Formula : | C6H5ClN4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HXUMCGPDKBIKSQ-UHFFFAOYSA-N |
M.W : | 200.65 | Pubchem ID : | 21098062 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.41 |
TPSA : | 79.76 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.13 cm/s |
Log Po/w (iLOGP) : | 1.44 |
Log Po/w (XLOGP3) : | 1.97 |
Log Po/w (WLOGP) : | 1.73 |
Log Po/w (MLOGP) : | 0.6 |
Log Po/w (SILICOS-IT) : | 2.26 |
Consensus Log Po/w : | 1.6 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.81 |
Solubility : | 0.308 mg/ml ; 0.00153 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.27 |
Solubility : | 0.108 mg/ml ; 0.000537 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.29 |
Solubility : | 0.104 mg/ml ; 0.000519 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.05 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
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 |
---|---|---|
67% | With [2,2]bipyridinyl; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 60.0℃; for 18.0h; | A suction flask was charged with <strong>[100859-88-9]3-chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine</strong> (0.2 g, 0.99 mmol), cycloboronic acid (0.17 g, 1.99 mmol), 2,2'-bipyridine (0.15 g, 0.99 mmol), and Na2CO3 (0.21 g, 1.99 mmol). Dichloroethane (10 ml) was added thereto, and nitrogen (N2) was bubbled for 10 minutes. Cu(OAc)2 (0.18 g, 0.99 mmol) was added thereto, and N2 was bubbled for 1 minute, which was stirred at 60C for 18 hours. The temperature was lowered to room temperature, and it was filtered with ethyl acetate and then concentrated. It was extracted with ethyl acetate and a IN aqueous hydrochloric acid solution, dried over MgSO4, filtered under reduced pressure, and concentrated. It was subjected to column chromatography to obtain 0.16 g of the target compound (yield: 67%). MS (ESI) m/z 241.1, 243.2 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 1H), 3.82-3.75 (m, 1H), 2.67 (s, 3H), 1.36-1.33 (m, 2H), 1.18-1.14 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With caesium carbonate; In N,N-dimethyl-formamide; at 80.0℃; for 5.0h; | 3-Chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (70 mg, 0.49 mmol) was dissolved in an N,N-dimethylformamide solvent (63 ml). Cesium carbonate (243 mg, 0.74 mmol) and 2,2,2-trifluoroethyl methane sulfonate (70.0 ml, 0.59 mmol) were added thereto, which was stirred at 80C for 5 hours. The temperature was lowered to room temperature, and it was extracted with water and ethyl acetate. The organic layer was dried over MgSO4, filtered under reduced pressure, and concentrated. It was subjected to column chromatography to obtain 48.3 mg of the target compound (yield: 48%). MS (ESI) m/z 282.8, 285.0 [M+H]+; 1H NMR (300 MHz, Acetone-d6) δ 9.09 (s, 1H), 5.27 (q, J = 8.7 Hz, 2H), 2.66 (s, 3H). |
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