Structure of 4269-17-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 4269-17-4 |
Formula : | C13H7BrO |
M.W : | 259.10 |
SMILES Code : | O=C1C2=C(C3=C1C=CC=C3)C(Br)=CC=C2 |
MDL No. : | MFCD22988837 |
InChI Key : | YWYZCXNQMZOYHM-UHFFFAOYSA-N |
Pubchem ID : | 255651 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 63.01 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.39 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.75 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.66 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.27 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.31 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.47 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.4 |
Solubility | 0.0103 mg/ml ; 0.0000397 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.8 |
Solubility | 0.041 mg/ml ; 0.000158 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.93 |
Solubility | 0.000304 mg/ml ; 0.00000117 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.22 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.44 |
* 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 |
---|---|---|
72% | 9- (2-bromo-phenyl) -9H- carbazole (9- (2-bromophenyl) -9H-carbazole, 3-1) was dissolved 9.4g (29mmol) in 80mL of anhydrous tetrahydrofuran cooled to -78 It was. Normal to the cooled solution - and then put the semi-butyl lithium (2.5M) 13mL (32mmol) slowly and stirred for 30 minutes at the same temperature. 4-bromo--9H- fluorene-9-one (4-bromo-9H-fluoren-9-one) To a mixture of the cold put 7.5g (29mmol, 3-2). When the reaction is complete, the mixture gives the temperature up to room temperature and stirred was added a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate and treated with anhydrous magnesium sulfate and concentrated after filtration. It was added to an excess of hexane and a small amount of ethyl acetate to the compound of the concentrated state after stirring was filtered to give 10.6g of the desired compound 3-3 (72%) of white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | A solution of the intermediate a (6.96 g) in purified THF (300 ml) was cooled to -78 C. A 2.5 M hexane solution of n-butyllithium (8.64 ml) was gradually added dropwise. After stirring at the same temperature for 30 min, 4-bromo-9-fluorenone (6.08 g) was added. After stirring at the same temperature for 40 min and further stirring at ordinary temperature for 3 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed. The obtained solid was dispersed in ethanol and the dispersion was stirred for one day. The solid collected by filtration was vacuum-dried to obtain an intermediate (10.12 g, 97% yield), which was then dispersed in 10 ml of acetic acid. After adding 10 drops of concentrated sulfuric acid, the dispersion was refluxed for 4 h. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate B (9.49 g, 97% yield). MS: [M+H]+=563 | |
97% | A solution of the intermediate a (6.96 g) in purified THF (300 ml) was cooled to -78 C. A 2.5 M hexane solution of n-butyllithium (8.64 ml) was gradually added dropwise. After stirring at the same temperature for 30 min, 4-bromo-9-fluorenone (6.08 g) was added. After stirring at the same temperature for 40 min and further stirring at ordinary temperature for 3 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed. The obtained solid was dispersed in ethanol and the dispersion was stirred for one day. The solid collected by filtration was vacuum-dried to obtain an intermediate (10.12 g, 97% yield), which was then dispersed in 10 ml of acetic acid. After adding 10 drops of concentrated sulfuric acid, the dispersion was refluxed for 4 h. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate B (9.49 g, 97% yield). MS: [M+H]+=563 | |
97% | Intermediate a (6.96 g) was dissolved in purified THF (300 ml) and then cooled to -78 C. A 2.5 M solution of n-butyllithium in hexane (8.64 ml) was slowly added dropwise. After stirring at the same temperature for 30 minutes, 4-bromo-9-fluorenone, (6.08 g) was added. After stirring at the same temperature for 40 minutes, the temperature was raised to room temperature and further stirred for 3 hours, and then an aqueous solution of ammonium chloride was added to terminate the reaction. After extracting organic matter with ethyl ether, the extract was dried over anhydrous magnesium sulfate, then ethyl ether was removed. The resulting solid was dispersed in ethanol and stirred for 1 day. The solid filtered off was dried under vacuum to obtain 10.12 g (97% yield) of intermediate. The obtained intermediate was dispersed in 10 ml of acetic acid, 10 drops of concentrated sulfuric acid was added thereto, and the mixture was refluxed for 4 hours. The obtained solid was filtered off, washed with ethanol and then dried under vacuum to obtain 9.49 g (97% yield) of Intermediate B. |
65% | 9-(2-Bromophenyl)carbazole (12.81 g, 40 mmol)Add in a three-necked flask,Stir and dissolve with 200 mL of anhydrous tetrahydrofuran.Nitrogen protection,Cool down to -78 C,Then slowly add dropwise 16 mL of 2.5 M butyl lithium solution.Stir for half an hour after adding.Next 4-bromo-l-ketone (10.36 g, 40 mmol)a tetrahydrofuran solution is dropped into the reaction solution,After the drop, rise to room temperature,Stir the reaction for 2 hours,Quenched by adding saturated ammonium chloride solution,Add water,Concentrated organic phase,Get a yellow oil,Add this oilA mixture of 100 mL of HAc and 20 mL of HCl was stirred and refluxed for 12 hours.Cool, then add saturated brine,And extracted with dichloromethane,The organic phase is obtained.Wash the organic phase three times with water,Evaporate to remove the solvent,The residue was recrystallized from DCM/PE.The compound 5-1 (12.56 g, yield 65%) was obtained as a white solid. |
Tags: 4269-17-4 synthesis path| 4269-17-4 SDS| 4269-17-4 COA| 4269-17-4 purity| 4269-17-4 application| 4269-17-4 NMR| 4269-17-4 COA| 4269-17-4 structure
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