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CAS No. : | 1022150-57-7 | MDL No. : | MFCD16660190 |
Formula : | C18H13N7S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BCZUAADEACICHN-UHFFFAOYSA-N |
M.W : | 359.41 | Pubchem ID : | 24779724 |
Synonyms : |
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.06 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 99.13 |
TPSA : | 99.09 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.8 cm/s |
Log Po/w (iLOGP) : | 2.45 |
Log Po/w (XLOGP3) : | 2.38 |
Log Po/w (WLOGP) : | 3.22 |
Log Po/w (MLOGP) : | 2.5 |
Log Po/w (SILICOS-IT) : | 1.8 |
Consensus Log Po/w : | 2.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.05 |
Solubility : | 0.0318 mg/ml ; 0.0000886 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.1 |
Solubility : | 0.0284 mg/ml ; 0.0000791 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.14 |
Solubility : | 0.000259 mg/ml ; 0.000000719 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.0 |
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 |
---|---|---|
64% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 100℃; for 22 h; | Method b; [0358] A solution of 6-bromoquinoline (550 mg, 2.64 mmol), diisopropylethylamine (1.13 niL, 6.46 mmol) in DMA (4 mL) under nitrogen was degassed by bubbling in nitrogen for 20 min. Tris(dibenzylideneacetone)dipalladium (105 mg, 0.108 mmol, Strem catalyst), Xantphos (125 mg, 0.216 mmol), and 6-(l-methyl-lH-pyrazol-4-yl)-[l,2,4]triazolo[4,3- ]pyridazine-3 -thiol (500 mg, 2.155 mmol) were added under a stream of nitrogen. The reaction mixture was stirred at 1000C for 22h, with disappearance of the solid suspension. The reaction mixture was cooled to room temperature and filtered through a plug of silica gel, using DMF as eluent. The organics were then directly poured onto ice/water mixture and left standing for 15 min. The precipitate was filtered and washed with water. The resulting cake was grinded in diethyl ether, filtered, and dried in vacuo to yield 770 mg of a yellow solid. The solid was stirred in refluxing isopropanol for Ih, filtered, washed with isopropanol, and dried in a vacuum oven at 7O0C for 3 days to provide 500 mg of 6-[6-(l- methyl-lH-pyrazol-4-yl)-[l,2,4]triazolo[4,3-6]pyridazin-3-ylsulfanyl]-quinoline as a yellow solid with 8percent impurity (64percent yield). |
58% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 23 h; | Example 4: 6-[6-(l-Methyl-lH-pyrazol-4-yl)-[l,2,4]triazoIo[4,3-^]pyridazin-3- ylsulfanyl]-quinoline (Compound 4); Method a; [0356] A solution of 6-bromoquinoline (45 mg, 0.215 mmol), diisopropylethylamine (0.075 mL, 0.43 mmol) in DMF (1 mL) under nitrogen was degassed by bubbling in nitrogen for 5 min. Tris(dibenzylideneacetone)dipalladium (11 mg, 0.011 mmol), Xantphos (13 mg, 0.022 mmol), and 6-(l-methyl-lH-pyrazol-4-yl)-[l,2,4]triazolo[4,3-]pyridazine-3- thiol (50 mg, 0.215 mmol) were added, and the mixture was degassed for another 5 min. The reaction mixture was stirred at 1000C for 23 h. More palladium catalyst (11 mg) and ligand (13 mg) were added after 6 h. The reaction mixture was cooled to room temperature, filtered through a 0.45 um filter, and the crude mixture was purified directly by mass- triggered HPLC (5 - 95percent CH&3CN/H2O, 0.1percent HCOOH modifier) to provide 45 mg of 6-[6- (1 -methyl-1 H-pyrazol-4-yl)-[l ,2,4]triazolo[4,3-]pyridazin-3-ylsulfanyl]-quinoline as a yellow solid (58percent yield). |