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CAS No. : | 1256345-69-3 | MDL No. : | MFCD08704681 |
Formula : | C10H13BO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GDWZKERCECMYJX-UHFFFAOYSA-N |
M.W : | 208.02 | Pubchem ID : | 53216302 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 56.94 |
TPSA : | 66.76 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) : | -6.87 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.98 |
Log Po/w (WLOGP) : | -0.53 |
Log Po/w (MLOGP) : | 0.55 |
Log Po/w (SILICOS-IT) : | -0.16 |
Consensus Log Po/w : | 0.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.71 |
Solubility : | 4.03 mg/ml ; 0.0194 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.97 |
Solubility : | 2.23 mg/ml ; 0.0107 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.18 |
Solubility : | 1.37 mg/ml ; 0.00659 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.19 |
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 |
---|---|---|
Under a nitrogen atmosphere, 3-(3-(4-bromophenyl)propyl)-4-ethyl-lH-l,2,4-triazol-5(4H)- one (0.20 g, 0.65 mmol), Pd(PPh)4 (0.056 g, 0.065 mmol), KF (0.17 g, 2.84 mmol), (3-(2-ethoxy-2- oxoethyl)phenyl)boronic acid (0.296 g, 1.42 mmol), toluene (4 mL) and water (4 mL) were combined and the resulting mixture was stirred under nitrogen at 100 C for 16 hrs. The reaction mixture was then cooled to rt, diluted with EtOAc and washed with a 50% brine/50% water solution. The organic phase was separated, washed once more with brine, filtered through a Na2S04/paper plug, and the filtrate concentrated in vacuo. The residue was thus obtained was purified by column chromatography using a l%>-9%> gradient MeOH/DCM as eluent to afford 0.190 g of ethyl 2-(4'-(3-(4-ethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-3- yl)propyl)-[l,l'-biphenyl]-3-yl)acetate (contaminated with unreacted starting material which coeluted). This was used as is in the next step. [00154] Step 2; To a solution of ethyl 2-(4'-(3-(4-ethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-3-yl)propyl)- [l,l'-biphenyl]-3-yl)acetate (0.10 g, 0.25 mmol) in anhydrous CH3CN (4 mL) and Cs2C03 (0.25 g, 0.72 mmol) at rt was added 4-bromobenzyl bromide (0.076 g, 0.31 mmol). The resulting mixture was stirred at 65 C for 16 hrs. The mixture was diluted with EtOAc and a 50%> brine/50%) water solution. The organic extract was separated, washed once more with brine, filtered through a Na2S04/paper plug, and the filtrate concentrated in vacuo. The crude product thus obtained was used as is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 16h;Inert atmosphere; | Under a nitrogen atmosphere, 3-(3-(4-bromophenyl)propyl)-4-ethyl-lH-l,2,4-triazol-5(4H)- one (0.20 g, 0.65 mmol), Pd(PPh)4 (0.056 g, 0.065 mmol), KF (0.17 g, 2.84 mmol), (3-(2-ethoxy-2- oxoethyl)phenyl)boronic acid (0.296 g, 1.42 mmol), toluene (4 mL) and water (4 mL) were combined and the resulting mixture was stirred under nitrogen at 100 C for 16 hrs. The reaction mixture was then cooled to rt, diluted with EtOAc and washed with a 50% brine/50% water solution. The organic phase was separated, washed once more with brine, filtered through a Na2S04/paper plug, and the filtrate concentrated in vacuo. The residue was thus obtained was purified by column chromatography using a l%>-9%> gradient MeOH/DCM as eluent to afford 0.190 g of ethyl 2-(4'-(3-(4-ethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-3- yl)propyl)-[l,l'-biphenyl]-3-yl)acetate (contaminated with unreacted starting material which coeluted). This was used as is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 85℃; for 3h;Inert atmosphere; | General procedure: Step 1: To a solution of 3-(3-(3-bromophenyl)propyl)-l -(4-(tert-butyl)benzyl)-4-ethyl-lH-l ,2,4- triazol-5(4H)-one (250 mg, 0.55 mmol) in a mixture of DME (5 mL) and water (2 mL) was added potassium carbonate (191 mg, 1.38 mmol) and <strong>[1256345-69-3]3-ethoxycarbonylmethylphenylboronic acid</strong> (191 mg, 0.66 mmol). After sparging the mixture with nitrogen, Pd(PPh3)4 (30 mg, cat.) was added and the reaction heated at 85 C for 3 hrs. The reaction as allowed to cool, partitioned between EtOAc and water, the organic phase extracted, dried(MgSO i), filtered and evaporated in vacuo. The residue was purified on silica gel eluting with a gradient of 0 to 60% EtOAc in hexanes to afford the ester of the title compound |
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